Dimethyl Sulfide → HCID 19103244, compound

Participants

Reaction Steps

To a solution of 2-bromo-5-benzyloxy benzaldehyde dimethyl acetal (Tet. Lett., 22, 5027 (1981)) (52.2 g) in THF (600 mL), cooled to -78° C., was added dropwise a solution of n-BuLi (78 ml, 2.1M) in hexane. After 15 min. CuBr.SMe2 (32 g) was added in 3 portions. The reaction mixture was stirred at -78° C. until CuBr.SMe2 was dissolved (approx. 1 hr.), then benzoyl chloride (20 mL) was added dropwise. The cooling bath was removed and the reaction mixture was stirred at room temperature over night and was quenched with a saturated NH4Cl solution. The organic phase was diluted with Et2O, washed with H2O (3×), brine, dried (MgSO4) and evaporated to afford the title compound which was used as such for the next step.

Provenance & Evidence