Boron tribromide → 2,2,2-Trifluoro-1-(4-hydroxyphenyl)ethanone

Participants

Reaction Steps

To a cooled (−78° C.) solution of 2,2,2-trifluoro-4′-methoxyacetophenone (15 ml, 73 mmol) in DCM was added 1.0 M tribromoborane (73 ml, 73 mmol) drop wise. After the addition was completed, the reaction was slowly warmed to RT and stirred for overnight (15 h). At this point, reaction was completed by TLC. The product mixture was poured into ice water. The organic layer was washed with 10% aq Na2CO3, water and brine, dried over Na2SO4, filtered and concentrated. The residue was purified on silica gel column (5-40% EtOAc/hexane) to afford the title compound as a white crystalline solid. The major side product was a colorless oil with MS+=379.

Provenance & Evidence