1,3-Dibromobenzene → HCID 22328599, compound

Participants

Reaction Steps

To a stirred −78° solution of m-dibromobenzene (70.9 g, 0.3 mol) in 200 mL of dry THF under Ar was added 117 mL of 2.56 M n-BuLi (0.3 mol) in hexane over 10 min. After 30 min, p-methoxybenzaldehyde (27.2 g, 0.02 mol) in 50 mL of THF was added over 20 min. The solution was stirred for 1 hr at −78° (complete by tlc) prior to quenching with saturated aq. NH4Cl. After warming to 20°, the reaction was diluted 2 fold with EtOAc prior to washing with H2O followed by brine. After drying over Na2SO4 and concentration using a rotary evaporator, 103 g of 3-bromo-4′-methoxybenzhydrol was obtained as a yellow oil that was carried forward without further purification.

Provenance & Evidence