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

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.

1. additionAfter the addition
2. customAt this point, reaction
3. washThe organic layer was washed with 10% aq Na2CO3, water and brine
4. dry with materialdried over Na2SO4
5. filtrationfiltered
6. concentrationconcentrated
7. customThe residue was purified on silica gel column (5-40% EtOAc/hexane)

ORD record

ord-b02e7d90691f44f989c632718d6d8fde

Source dataset

uspto-grants-2010_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07745484B2