2-(Benzyloxy)-3-bromobenzaldehyde → (2-(Benzyloxy)-3-bromophenyl)(phenyl)methanol

Participants

Reaction Steps

A solution of 8 (8.6 g, 29.55 mmol, 1.0 equiv) in THF (220 mL) was cooled to ˜10° C. and 1M PhMgBr in THF (45 mL, 45 mmol, 1.5 equiv) was added slowly via syringe at <10° C. A pale yellow color initially developed that changed to light blue then back to pale yellow. The mixture was allowed to warm to room temperature and stirred 2 hr. The mixture was recooled to ˜0° C. and quenched by addition of saturated NH4Cl solution (100 mL). The mixture was partitioned between EtOAc (300 mL) and H2O (25 mL). The organic phase was washed with brine (200 mL), dried over Na2SO4, filtered and the solution concentrated under reduced pressure to give a yellow oil. The crude product was absorbed onto silica gel using DCM and dry-loaded on a column of silica gel (100 g) packed in heptanes. The column was eluted with heptanes (1 L), 5% EtOAc/heptanes (1 L) and 10% EtOAc/heptanes (2 L). Product fractions were concentrated under reduced pressure to give 8.7 g (80%) of 9 as a nearly colorless oil.

Provenance & Evidence