Carbon tetrabromide → HCID 22645499, compound

Participants

Reaction Steps

t-Butyl-3-(hydroxymethyl)-phenoxyacetate is dissolved in dichloromethane (1.3 L) at room temperature. Triphenylphosphine (127 g, 0.48 mol) is added with stirring, followed by dropwise addition of CBr4 (146 g, 0.44 mol). The resultant mixture is stirred for 1 hour at room temperature and then evaporated in vacuo. The residue (553 g) is adsorbed onto silica-gel (100 g) and then placed on a sintered glass funnel containing 700 g of silica gel. The column is eluted with hexane (2×4000 L) followed by 4:1 hexane/EtOAc (2×4000L). The hexane/EtOAc solutions are combined and evaporated in vacuo to provide t-butyl 3-(bromomethyl)-phenoxyacetate as a colorless oil. MS Found: M+18+:318, 320.

Provenance & Evidence