2-Bromo-1,4-benzenedimethanol

(2-bromo-4-hydroxymethylphenyl)methanol.png

(2-bromo-4-hydroxymethylphenyl)methanol;

 CAS 89980-92-7; 

2-Bromo-1,4-benzenedimethanol;

Molecular Formula: C8H9BrO2
Molecular Weight: 217.05986 g/mol

(2-Bromo-4-hydroxymethylphenyl)methanol (3).

To a solution of commercially available 2-bromoterephthalic acid (2) (575 g, 2.34 mol) in THF (5.75 L), a THF solution of BH3 (1.0 M, 5.86 L) was added at 0 °C dropwise for 2.5 h, and the mixture was stirred for 1 h at 0 °C. The mixture was gradually warmed up to 35 °C over 3.5 h. The reaction mixture was cooled to 0 °C and quenched by dropwise addition of MeOH (1.15 L) over 30 min. Then, the mixture was concentrated in vacuo. The residue was dissolved in MeOH (1.72 L), and then water (10.3 L) was added; the mixture was then stirred at 0 °C for 30 min. The off-white solid was filtered and washed with water (1.15 L × 3) and heptanes (2.30 L) to obtain 3 (426 g, 84%) as a white crystal;

mp 108–109 °C;

1H NMR (400 MHz, DMSO-d6) δ: 4.47 (2H, d, J = 5.6 Hz), 4.49 (2H, d, J = 5.4 Hz), 5.29 (1H, t, J = 5.6 Hz), 5.39 (1H, t, J = 5.4 Hz), 7.31 (1H, d, J = 7.8 Hz), 7.47 (1H, d, J = 7.8 Hz), 7.48–7.49 (1H, m);

13C NMR (100 MHz, DMSO-d6) δ: 61.9, 62.5, 120.8, 125.5, 127.9, 129.7, 139.1, 143.4;

HRMS (EI) calcd for C8H9BrO2 [M]+ 215.9786, found 215.9787.

1H NMR

1H NMR (400 MHz, DMSO-d6) δ: 4.47 (2H, d, J = 5.6 Hz), 4.49 (2H, d, J = 5.4 Hz), 5.29 (1H, t, J = 5.6 Hz), 5.39 (1H, t, J = 5.4 Hz), 7.31 (1H, d, J = 7.8 Hz), 7.47 (1H, d, J = 7.8 Hz), 7.48–7.49 (1H, m); 

13C NMR

13C NMR (100 MHz, DMSO-d6) δ: 61.9, 62.5, 120.8, 125.5, 127.9, 129.7, 139.1, 143.4;

MASS PREDICT

1H/13C PREDICT

J. Org. Chem.201681 (5), pp 2148–2153

DOI: 10.1021/acs.joc.5b02734

///////////c1(cc(c(cc1)CO)Br)CO

An efficient Passerini tetrazole reaction (PT-3CR)

Green Chemistry International

Graphical abstract: An efficient Passerini tetrazole reaction (PT-3CR)

An efficient Passerini tetrazole reaction (PT-3CR)

Green Chem., 2016, 18,3718-3721

DOI: 10.1039/C6GC00910G, Communication

Ajay L. Chandgude, Alexander Domling

A sonication accelerated, catalyst free, simple, high yielding and efficient method for the Passerini-type three-component reaction (PT-3CR) has been developed.

http://pubs.rsc.org/en/Content/ArticleLanding/2016/GC/C6GC00910G?utm_source=feedburner&utm_medium=feed&utm_campaign=Feed%3A+rss%2FGC+%28RSC+-+Green+Chem.+latest+articles%29#!divAbstract

A sonication accelerated, catalyst free, simple, high yielding and efficient method for the Passerini-type three-component reaction (PT-3CR) has been developed. It comprises the reaction of an aldehyde/ketone, an isocyanide and a TMS-azide in methanol : water (1 : 1) as the solvent system. The use of sonication not only accelerated the rate of the reaction but also provided good to excellent quantitative yields. This reaction is applicable to a broad scope of aldehydes/ketones and isocyanides.

An efficient Passerini tetrazole reaction (PT-3CR)

*
Corresponding authors
a
Department of Drug Design, University of Groningen, Antonius Deusinglaan 1, 9713 AV…

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Oxidation of refractory sulfur compounds with molecular oxygen over a Ce-Mo-O catalyst

Green Chemistry International


Oxidation of refractory sulfur compounds with molecular oxygen over a Ce-Mo-O catalyst

 Green Chem., 2016, Advance Article
DOI: 10.1039/C6GC01357K, Paper
Yawei Shi, Guozhu Liu, Bofeng Zhang, Xiangwen Zhang
A Ce-Mo-O catalyst showed remarkable performance for aerobic oxidative desulfurization without sacrificial agents at 100 [degree]C and atmospheric pressure.

Oxidation of refractory sulfur compounds with molecular oxygen over a Ce–Mo–O catalyst

Yawei Shi,a   Guozhu Liu,*a   Bofeng Zhanga and  Xiangwen Zhang*a  
*
Corresponding authors
a
Key Laboratory for Green Chemical Technology of Ministry of Education, School of Chemical Engineering and Technology, Collaborative Innovation Centre of Chemical Science and Engineering (Tianjin), Tianjin University, Tianjin 300072, China
E-mail: gliu@tju.edu.cnzhangxiangwen@tju.edu.cn
Fax: +86 22 27892340
Tel: +86 22 27892340
Green Chem., 2016, Advance Article

DOI: 10.1039/C6GC01357K

http://pubs.rsc.org/en/Content/ArticleLanding/2016/GC/C6GC01357K?utm_source=feedburner&utm_medium=feed&utm_campaign=Feed%3A+rss%2FGC+%28RSC+-+Green+Chem.+latest+articles%29#!divAbstract

A Ce–Mo–O catalyst prepared by a simple sol–gel method was proved to…

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Visible-light-activated copper(I) catalyzed oxidative Csp–Csp cross-coupling reaction: efficient synthesis of unsymmetrical conjugated diynes without ligands and base

Green Chemistry International

A novel visible-light-promoted copper-catalysed process for the Csp–Csp cross-coupling reaction of terminal alkynes at room temperature is described. The current photochemical method is simple, highly functional group compatible, and more viable towards the construction of bio-active 1,3-unsymmetrical conjugated diynes without the need of bases/ligands, additives and expensive palladium/gold catalysts.

Visible-light-activated copper(I) catalyzed oxidative Csp-Csp cross-coupling reaction: efficient synthesis of unsymmetrical conjugated diynes without ligands and base

Green Chem., 2016, Advance Article
DOI: 10.1039/C6GC01463A, Communication
Arunachalam Sagadevan, Ping-Chiang Lyu, Kuo Chu Hwang
An efficient and eco-friendly approach to Csp-Csp cross-coupling of terminal alkynes for the construction of unsymmetrical conjugated diynes via a visible-light-induced CuCl catalysed process at room temperature is described.
Communication

Visible-light-activated copper(I) catalyzed oxidative Csp–Csp cross-coupling reaction: efficient synthesis of unsymmetrical conjugated diynes without ligands and base

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Microbial cyclosophoraose as a catalyst for the synthesis of diversified indolyl 4H-chromenes via one-pot three component reactions in water

Green Chemistry International

Green Chem., 2016, 18,3620-3627
DOI: 10.1039/C6GC00137H, Paper
Someshwar D. Dindulkar, Daham Jeong, Eunae Cho, Dongjin Kim, Seunho Jung
A novel biosourced saccharide catalyst, microbial cyclosophoraose, a cyclic [small beta]-(1,2) glucan, was used for the synthesis of indolyl 4H-chromenes via a one pot three-component Knoevenagel-Michael addition-cyclization reaction in water under neutral conditions.

Microbial cyclosophoraose as a catalyst for the synthesis of diversified indolyl 4H-chromenes via one-pot three component reactions in water

 *corresponding authors
a
Institute for Ubiquitous Information Technology and Applications (UBITA) & Center for Biotechnology Research in UBITA (CBRU), Konkuk University, Seoul 143-701, South Korea
E-mail: shjung@konkuk.ac.kr
b
Nelson Mandela African Institution of Science and Technology, PO box 447, Arusha, Tanzania
c
Department of Bioscience and Biotechnology…

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GSK-2838232

New Drug Approvals

STR1

Figure imgf000135_0002

GSK-2838232

4-(((3aR,5aR,5bR,7aR,9S,11aR,11bR,13aS)-3a-((R)-2-((3-chlorobenzyl)(2-(dimethylamino)ethyl)amino)-1-hydroxyethyl)-1-isopropyl-5a,5b,8,8,11a-pentamethyl-2-oxo-3,3a,4,5,5a,5b,6,7,7a,8,9,10,11,11a,11b,12,13,13a-octadecahydro-2H-cyclopenta[a]chrysen-9-yl)oxy)-2,2-dimethyl-4-oxobutanoic acid.

28-Norlup-18-en-21-one, 3-(3-carboxy-3-methyl-1-oxobutoxy)-17-[(1R)-2-[[(4-chlorophenyl)methyl][2-(dimethylamino)ethyl]amino]-1-hydroxyethyl]-, (3β)-

Phase I

Glaxosmithkline Llc INNOVATOR

Mark Andrew HATCHER, Brian Alvin Johns,Michael Tolar Martin, Elie Amine TABET, Jun Tang

A reverse transcriptase inhibitor potentially for the treatment of HIV infection.

GSK-2838232; GSK-8232; 2838232

CAS No. 1443460-91-0

C48H73ClN2O6,809.56

SYNTHESIS

PART 1

STR1

PART2

STR1

PART3

STR1

PART 4

STR1

AND UNWANTEDISOMER SHOWN BELOW

PART5

STR1

GSK2838232 is a novel human immune virus (HIV) maturation inhibitor being developed for the treatment of chronic HIV infection. GSK2838232 is a betulin derivative

Human immunodeficiency virus type 1 (HIV-1 ) leads to the contraction of acquired immune deficiency disease (AIDS). The number of cases of HIV continues to rise, and currently over twenty-five million individuals worldwide suffer from the virus. Presently, long-term suppression of viral replication with antiretroviral drugs is the only option for treating HIV-1 infection. Indeed, the U.S. Food and Drug Administration has approved twenty-five drugs over six…

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Selective reduction of aldehydes and ketones to alcohols with ammonia borane in neat water

Green Chemistry International

Graphical abstract: Selective reduction of aldehydes and ketones to alcohols with ammonia borane in neat water

Chemoselective reduction of various carbonyl compounds to alcohols with ammonia borane (AB), a nontoxic, environmentally benign, and easily handled reagent, in neat water was achieved in quantitative conversions and high isolated yields. Interestingly, α- and β-keto esters were selectively reduced to corresponding hydroxyl esters by AB, while diols were obtained when sodium borohydride was used as a reducing agent. The procedure is also compatible with the presence of a variety of base-labile protecting groups, such as tosyl, acetyl, benzoyl, ester groups, and acid-labile protecting groups such as trityl and TBDMS groups, and others, such as the unsaturated double bond, nitro and cyano groups. Finally, a kilo scale reaction of methyl benzoylformate with AB was conducted in water and gave methyl mandelate in 94% yield.

Selective reduction of aldehydes and ketones to alcohols with ammonia borane in neat water

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