(4-BROMO-3-FLUOROPHENYL)METHANOL

General procedure: BHTo a solution of commercially available 4-bromo-3-fluoro-benzoic acid (SI-2) (11 g, 50 mmol) in THF (250 mL) was added BHStep 1 (MT-Si):Boranmethyl sulfide in ether (5.0 M; 38.3 mL, 191.8 mmol) was added to a solution of 4- bromo-3-fluorobenzoic acid (21.0 g, 95.9 mmol) in dry tetrahydrofuran (250 mL) at 0°C and the reaction mixture was stirred at room temperature for 6 h. The reaction was quenched with saturated sodium hydrogen carbonate solution, extracted with ethyl acetate, and the combined organic layers were washed with water, brine; dried over anhydrous sodium sulfate and filtered. The solvent was evaporated under vacuum to afford 18 g (91 .6percent) of MTSi as a colorless liquid, further used without any purification.Step A: (4-Bromo-3-fluorophenyl methanolA 0°C solution of 4-bromo-3-fluoro benzoic acid (2.3 g, 10.50 mmol) in dry THF (52.5 ml) is treated with borane tetrahydrofuran complex (15.75 ml of a 1 M solution in THF, 15.75 mmol) and the resulting mixture stirred at RT for 72 hours. The mixture is then quenched with IN HC1, stirred for 20 minutes, then extracted with DCM. Concentration and silica gel chromatography (10-50percent EtOAc/hexanes) yields the title compound 1.87 g (87 percent yield) as colorless needles. 1H NMR (500 MHz, CDC1A ooc solution of 4-bromo-3-fluoro benzoic acid (2.3 g, 10.50 mmol) in dry THF (52.5ml) is treated with borane tetrahydrofuran complex (15.75 ml of a 1M solution in THF, 15.75mmol) and the resulting mixture stirred at RT for 72 hours. The mixture is then quenched with20 IN HCl, stirred for 20 minutes, then extracted with DCM. Concentration and silica gelchromatography (10-50percent EtOAc/hexanes) yields the title compound 1.87 g (87percent yield) ascolorless needles. 1H NMR (500 MHz, CDCh) 8 7.55 (m, IH), 7.04 (d, J9.4 Hz, IH), 7.04 (d, J8.3 Hz, IH), 4.70 (d, 2H).To a suspension of sodium borohydride (10.4 g, 0.27 mol) in tetrahydrofuran (200 mL) was added boron trifluoride etherate (44.3 mL, 0.36 mol) followed by 4-bromo-3- fluoro-benzoic acid (10.0 g, 0.04 mol) in THF (200 mL) at ice temperature. The mixture was allowed to stir at room temperature over a period of 2 h. The resulting reaction mixture was quenched with methanol and methanol was removed under reduced pressure. The residue obtained upon evaporation of methanol was diluted with ethyl acetate (1.0 L), washed with water (700 mL), dried over sodium sulphate and concentrated to give (4- bromo-3-fluoro-phenyl)-methanol as off-white solid (7.9 g, 84percent)To a suspension of sodium borohydride (10.4 g, 0.27 mol) in tetrahydrofuran (200 mL) was added boron trifluoride etherate (44.3 mL, 0.36 mol) followed by 4-bromo-3-fluoro-benzoic acid (10.0 g, 0.04 mol) in THF (200 mL) at ice temperature.A suspension of 4-bromo-3-fluorobenzoic acid (84) (1.61 g, 7.35 mmol) in anhydrous THF (10 mL, then 4x 3 mL to rinse) under NR. Synthesis of (6S)-6-{[2-fluoro-4'-(trifluoromethoxy)[1, 1'-biphenyl]-4-yl]methoxy}-2-nitro-6, 7-dihydro-5H-imidazo[2, 1-6][1, 3]oxazine (15) by the method of Scheme 11 A suspension of 4-bromo-3-fluorobenzoic acid (84) (1.61 g, 7.35 mmol) in anhydrous THF (10 mL, then 4.x.3 mL to rinse) under NStep i :Solid NaBHSolid NaBHTo a solution of 4-bromo-3-fluorobenzaldehyde (10 g, 49.3 mmol) and NaBHTo a solution of 4-bromo-3-fluorobenzaldehyde (10 g, 49.3 mmol) and NaBHTo a solution of 4-bromo-3-fluoro-benzoic acid methyl ester (5.3 g, 22.9 mmol) in dry THF (60 mL) was added diisobutylaluminum hydride (30 mL) dropwise, This mixture was stirred overnight at room temperature until the starting material had been consumed, quenched with saturated aqueous potassium tartrate solution and extracted with ethyl acetate (3.x.50 mL). The combined organic layer was washed with brine, dried with Na

Molecular Weight:205.02
XLogP3:1.8
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:1
Exact Mass:203.95861
Monoisotopic Mass:203.95861
Topological Polar Surface Area:20.2
Heavy Atom Count:10
Complexity:110
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes