3-Bromo-4-chlorobenzenemethanol

A. (3-Bromo-4-chloro-phenyl)-methanolTo a mixture of 3-bromo-4-chloro-benzoic acid (10.0 g, 42.5 mmol) in THF (50 mL) under nitrogen at 0 °C is added 1 .0 M solution of borane.THF (55.3 mL, 55.3 mmol). After stirring at ambient temperature overnight the reaction is poured into a mixture of NaHCO3/HGeneral procedure: 3-bromo-4-chlorobenzoic acid (34.2 g, 145.25 mmol) was dissolved in THF (250 ml)and cooled to 0 °C, to this was added borane-methyl sulfide complex (153 ml, 305.02 mmol) and the reaction was warmed to room temperature and stirred overthe weekend. The reaction was very carefully quenched with saturated NaExample 6, Step 1To a solution of 3-bromo-4-benzoic acid 6-1 (4.0 g, 17.0 mmol) in anhydrous TI{F (18 mL) was slowly added BH3.DMS (1.6 g, 20.4 mmol) at 0°C then the reaction was refluxed at 80°C for 90 mm. The mixture was cooled and concentrated in vacuo, diluted with water and extracted with DCM. The organic layer was washed with saturated aqueous sodium bicarbonate solution then brine, dried over Na2SO4 and concentrated in vacuo. The residue waspurified by chromatography over silica gel (eluting with hexanes/EtOAc 100:0 to 0:100) to afford 3.4 g (90percent) of intermediate 6-2.B. Methanesulfonic acid 3-bromo-4-chloro-benzyl esterO I I?^ l l OO I To a mixture of 3-bromo-4-chloro-phenyl)-methanol (6.0 g, 27.1 mmol) in THF (50 mL ) under nitrogen at Oo C is added triethyl amine (3.6 g, 35.3 mmol) followed by methanesulfonyl chloride (4.0 g, 35.3 mmol). After stirring at ambient temperature for 1 h the reaction is poured into a mixture of NaHCO3/H2O/ice and extracted with EtOAc. The organic layer is washed with saturated aqueous NaCI, dried over MgSO4, filtered and concentrated in vacuo to provide the desired product (8.0 g, 99%) as a white solid.1 H NMR (300 MHz, CDCI3) delta 7.49 (m, 1 H), 7.49 (m, 1 H), 7.28 (m, 1 H), 5.17 (s, 2H), 3.00 (s, 3H).

Molecular Weight:221.48
XLogP3:2.4
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:1
Rotatable Bond Count:1
Exact Mass:219.92906
Monoisotopic Mass:219.92906
Topological Polar Surface Area:20.2
Heavy Atom Count:10
Complexity:110
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes