Carbon tetrabromide → HCID 67069911, compound

Participants

Reaction Steps

To a solution of 5-bromo-3-tert-butyl-2-methoxybenzaldehyde (0.30 g, 1.1 mmol; CASRN 417715-87-8) in EtOH (5 mL) at 0° C. was added NaBH4 (0.042 g, 1.1 mmol). The mixture was stirred for 1 h, and partitioned between 1N HCl and Et2O. The ether layer was evaporated, and the crude benzyl alcohol was dissolved in DCM and treated sequentially with CBr4 (0.55 g, 1.7 mmol) and PPh3 (0.45 g, 1.7 mmol). After stirring 2 h at RT, the reaction mixture was concentrated, and the crude product was purified by SiO2 chromatography eluting with EtOAc/hexane to afford 0.34 g (90%) 5-bromo-1-bromomethyl-3-tert-butyl-2-methoxybenzene (114).

Provenance & Evidence