(3-CHLORO-5-NITROPHENYL)METHANOL

To a stirred solution of 3-chloro-5-nitrobenzoic acid (5.00 g; 24.8 mmol; ABCR GmbH & CO. KG) in THF (48 mL) at 0°C was added a 1M solution of borane-THF complex in THF (99.2 mL; 99.2 mmol). The mixture was allowed to react at RT overnight. Then, MeOH was cautiously added to the stirred mixture while cooling with an ice bath. The batch was diluted with ethyl acetate and washed with aqueous sodium hydroxide solution (IN) and saturated aqueous sodium chloride solution. The organic phase was dried (sodium sulfate), filtered and concentrated. The residue was purified by chromatography hexane / ethyl acetate 50 percent to 100 percent) to give the pure product (4.22 g; 22.5 mmol). NMR (400MHz, CDC1(iii) General procedure: To a stirring solution of 2, 3-difluoro-5-nitrobenzoic acid (Butt Park Ltd.; 9.00 g; 44.3 mmol) in THF at 0C was added a 1M solution of borane-tetrahydrofuran complex in THF (177.3 mL; 177.3 mmol). The mixture was allowed to react at RT overnight. Then, MeOH was cautiously added to the stirred mixture while cooling with an ice bath. The batch was diluted with ethyl acetate and washed with aqueous sodium hydroxide solution (IN) and saturated aqueous sodium chloride solution. The organic phase was dried (sodium sulfate), filtered and concentrated. The residue was purified by chromatography (hexane to hexane / ethyl acetate 1 :2) to give the pure product (8.20 g; 43.4 mmol). NMR (400MHz, CDC13, 300K) delta = 8.26 (m, 1H), 8.03 (m, 1H), 4.89 (br, 2H), 2.13 (br, 1H).To a stirring solution of To a stirred solution of 3-chloro-5-nitrobenzoic acid (5.00 g; 24.8 mmol; ABCR GmbH & CO. KG) in THF (48 mL) at 0C was added a 1M solution of borane-THF complex in THF (99.2 mL; 99.2 mmol). The mixture was allowed to react at RT overnight. Then, MeOH was cautiously added to the stirred mixture while cooling with an ice bath. The batch was diluted with ethyl acetate and washed with aqueous sodium hydroxide solution (IN) and saturated aqueous sodium chloride solution. The organic phase was dried (sodium sulfate), filtered and concentrated. The residue was purified by chromatography hexane / ethyl acetate 50 % to 100 %) to give the pure product (4.22 g; 22.5 mmol). NMR (400MHz, CDC13, 300K) delta = 8.13 (m, 2H), 7.71 (s, 1H), 4.81 (m, 2H), 2.00 (br, 1H).Structural formula STR46 Step 1. Synthesis of 3-chloro-5-nitrobenzyl methanesulfonate To a solution of 92 mg of (i) 3-Chloro-5-N, N-dimethylaminobenzyl Alcohol To a solution of

Molecular Weight:187.58
XLogP3:1.5
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:1
Exact Mass:187.0036207
Monoisotopic Mass:187.0036207
Topological Polar Surface Area:66
Heavy Atom Count:12
Complexity:171
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes