2-BROMO-5-CHLOROBENZYL ALCOHOL

Compound 17-2 (0420) Compound 17-1 (5.0 g, 21.23 mmol) was added to BHB.l. (2-bromo-5-chloro-phenyl)-methanol:Starting from 2-bromo-5-chlorobenzoic acid (158.0 g; commercial) and proceeding in analogy to Procedure I, the title compound was obtained, without additional purification, as a white solid (146.0 g; 98percent yield).1H NMR (d6-DMSO) δ: 7.58 (d, J = 8.5 Hz, 1H); 7.52-7.49 (d, J = 2.8 Hz, 1H); 7.26 (dd, J = 8.5, 2.8 Hz, 1H); 5.56 (t, J = 5.7 Hz, 1H); 4.47 (d, J = 5.7 Hz, 2H). Procedure I (reduction of carboxylic acid):A solution of the acid (1.0 mmol; 1.0 eq.) in dry THF (4 mL), under inert atmosphere (NTo a solution of 2-bromo-5-chlorobenzoic acid (5.49 g, 23.3 mmol) in anhydrous THF (70 mL) under nitrogen was added dropwise a BHTo a solution of 2-bromo-5-chlorobenzoic acid (5.49 g, 23.3 mmol) in anhydrous THF (70 mL) under nitrogen was added dropwise a BHStep 1 : Preparation of (2-bromo-5-chloro-phenyl)methanol (A) A solution of borane-tetrahydrofuran complex in THF (0.15 L, 1.5 eq) was added dropwise to a solution of 2-bromo-5-chlorobenzoic acid (24 g) in anhydrous tetrahydrofuran (0.24 L) at 0°C and under argon atmosphere. The reaction mixture was stirred at room temperature for 16 h, before being slowly poured onto 0.10 L of a 2N aqueous solution of hydrogen chloride at 0°C. The mixture was stirred for 15 minutes and the volatiles were removed under reduced pressure. The aqueous layer was extracted with ethyl acetate and the combined organic layers were washed with a IN aqueous solution of sodium hydroxide and then water. After drying over sodium sulfate, filtration and concentration under reduced pressure, the crude product was purified by column chromatography; 23.2 g; M.p. 79-80 °C.A solution of the acid (1.0 mmol; 1.0 eq.) in dry THF (4 mL) in a round-bottomed flask, under inert atmosphere (NStep 1: (2-Bromo-5-chlorophenyl)methanol PREPARATION 172 (2-Bromo-5-chlorophenyl)methanol Sodium borohydride (0.17 g, 4.56 mmol) was suspended in 15 ml methanol. 2-Bromo- 5-chlorobenzaldehyde (1 g, 4.56 mmol) dissolved in 10 ml methanol was added drop- wise and the reaction mixture was stirred at room temperature overnight. The solvent was evaporated under reduced pressure and the residue was re-dissolved in ethyl acetate. The organics were washed sequentially with water and brine. The organic phase was dried over sodium sulphate, filtered and concentrated under reduced pressure to give 0.97 g (4.34 mmol, 95percent) of the title compound as a white solid. Purity 99percent. Example 73 Step 1. Synthesis of (2-bromo-5-chloro-phenyl)methoxy-tert-butyl-dimethyl-silane (1Ab) To a solution of

Molecular Weight:221.48
XLogP3:1.9
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