5-Benzyloxy-2-bromotoluene → HCID 70856270, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 5-benzyloxy-2-bromotoluene (1 g, 3.61 mmol) in THF (10 ml) was added 2-tert-butoxy-2-oxoethylzinc chloride (18.04 ml, 9.02 mmol). Nitrogen gas bubbled through the mixture for 10 min. then Pd2(dba)3 (0.165 g, 0.180 mmol) and X-PHOS (0.172 g, 0.361 mmol) were added and the resulting mixture heated at 60° C. for 50 min. The mixture was cooled, diluted with ethyl acetate (20 mL), washed with aqueous ammonium chloride (saturated, 1×15 mL), dried over MgSO4, filtered and the solvent evaporated under reduced pressure. The residue was purified by column chromatography on silica gel (Biotage 50M), using a gradient eluant of EtOAc/Hexane (0-20%) to afford the title compound. LC/MS (m/z): 335 (M+Na)+.

Provenance & Evidence