Diisobutylaluminum hydride → (4-Bromo-3,5-dichlorophenyl)methanol

Participants

Reaction Steps

DIBAL-H (1M in toluene, 66 mL, and 66.0 mmol) was added dropwise to a stirred solution of methyl 4-bromo-3,5-dichlorobenzoate (7.5 g, 26.0 mmol) in THF (50 mL) at −78° C. The reaction mixture was allowed to warm toward ambient temperature and stirred for 6 h. The reaction mixture was poured into ice-water and extracted with CH2Cl2. The organic layer was washed with brine followed by water, dried (Na2SO4), filtered and concentrated to afford 6.0 g of a mixture of (4-bromo-3,5-dichlorophenyl)methanol and 4-bromo-3,5-dichlorobenzaldehyde—as an off white solid which was taken to next step without purification.

Provenance & Evidence