4-(5-broMo-2-chlorobenzyl)phenol

To a solution of 4-bromo-1-chloro-2-(4-ethoxy-benzyl)-benzene (10.0 g, 30.71 mmol) in dichloromethane (40.0 mL) cooled to 0 degrees Celsius under nitrogen was added drop- wise over 30 minutes a 1 M solution of boron trichloride in dichloromethane (34 mL, 34.0 mmol). After the addition was complete, the reaction was allowed to warm to room temperature overnight (-16 hours). The reaction mixture was cooled to 0 degrees Celsius and an aqueous solution of 1 N hydrochloric acid was added. The resulting mixture was stirred for 30 minutes and then extracted using dichloromethane. The organic layer was separated and the aqueous layer was extracted two times with dichloromethane. The combined organic layers were dried over magnesium sulfate, filtered and concentrated under reduced pressure. The TLC showed only 50percent conversion. The crude material was redissolved in dichloromethane (40 mL), cooled to 0 degrees Celsius, and a 1M solution of boron tribromide in dichloromethane (31 mL, 31 mmol) was added dropwise. The reaction mixture was allowed to warm to room temperature over the weekend (-55 hours). The reaction mixture was cooled to 0 degrees Celsius and an aqueous solution of 1 N hydrochloric acid was added dropwise. The resulting mixture was stirred for 30 minutes and then extracted usingdichloromethane. The organic layer was separated and the aqueous layer was extracted two times with dichloromethane. The combined organic layers were dried over magnesium sulfate, filtered and concentrated under reduced pressure. The reaction was purified by flash chromatography over silica gel using the ISCO automated chromatography unit (120 g silica gel column) and eluting with a gradient of 0 to 100percent ethyl acetate in heptane. 9 g (98percent yield) of the desired product obtained as a white solid.To a 500 ml vial was added 5-bromo-2-chloro-4'-ethoxydiphenylmethane (III-1) (16 g, 4.95 mmol) and dichloromethane (200 ml). To the reaction system, 50 ml of a 1 mol/L boron tribromide dichloromethane solution was added, and after reacting for 1 hour, the starting material was consumed by TLC, and the reaction was completed. The system was poured into ice water and adjusted to pH 7 with sodium bicarbonate.The organic phase is separated and dried.Evaporation to obtain the target 15g (95.0percent).To a stirred solution of 4-bromo-l-chloro-2-(4-ethoxybenzyl)benzene (intermediate B) (3.0 g, 9.3 mmol) in dichloromethane (20 mL) was added BBr3 (IM in dichloromethane, 18.5 mL, 18.5 mmol) under the temperature of -78To a stirred solution of Example IB (747 g, 2.31 mol) in dichloromethane was added boron tribromide (1.15 kg, 4.62 mol) slowly at -78 To a stirred solution of 4-bromo-l-chloro-2-(4-ethoxybenzyl)benzene (747 g, 2.31 mol) in dichloromethane was added boron tribromide (1.15 kg, 4.62 mol) slowly at -78 °C. The reaction mixture was allowed to rise to room temperature. When the reaction was complete as measure by TLC, the reaction was quenched with water. The mixture was extracted with dichloromethane. The organic layer was washed with aqueous solution of saturated sodium bicarbonate, water, brine, dried over NaPreparation of 4-(5-bromo-2-chlorobenzyl)phenol (3)[0101] To a stirred solution of 4-bromo-l-chloro-2-(4-ethoxybenzyl)benzene (747 g, 2.31 mol) in dichloromethane was added boron tribromide (1.15 kg, 4.62 mol) slowly at -78 °C. The reaction mixture was allowed to rise to room temperature. When the reaction was complete as measure by TLC, the reaction was quenched with water. The mixture was extracted with dichloromethane. The organic layer was washed with aqueous solution of saturated sodium bicarbonate, water, brine, dried over NaStep 4: Synthesis of 4-(5-bromo-2-chlorobenzyl)phenol:To a stirred solution of (5-bromo-2-chlorophenyl)(4- hydroxyphenyl)methanone (step 3, 41 g) in dichloromethane (150 ml) and acetylnitrile (1: 1), Et

Molecular Weight:297.57
XLogP3:4.8
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:1
Rotatable Bond Count:2
Exact Mass:295.96036
Monoisotopic Mass:295.96036
Topological Polar Surface Area:20.2
Heavy Atom Count:16
Complexity:216
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes