2-Bromobenzaldehyde → 1-(2-Bromophenyl)-2,2,2-trifluoroethan-1-ol

To a solution of 2-bromobenzaldehyde (27.0 g, 146.5 mmol) and trimethylsilyl-trifluoromethane (25.0 g, 175.8 mmol) in tetrahydrofuran (300 ml) was added drop-wise tetrabutylammonium fluoride (1 M in tetrahydrofuran, 5 ml, 5 mmol) at 0° C. After the addition, the mixture was stirred at room temperature for 2 hours. Further tetrabutylammonium fluoride hydrate (49.0 g, 175.8 mmol) was added and the mixture was stirred for 30 minutes. The solvent was evaporated in vacuo. The residue was dissolved in dichloromethane (200 ml) and washed with hydrochloric acid (2N aqueous solution) (4×100 ml). The organic layer was separated, washed with Na2CO3 (10% aqueous solution) (50 ml), dried over anhydrous MgSO4 (s), filtered and evaporated in vacuo to afford the crude title compound as a yellow oil (45.0 g, ˜100%).

1. additionAfter the addition
2. stirringthe mixture was stirred for 30 minutes
3. customThe solvent was evaporated in vacuo
4. dissolutionThe residue was dissolved in dichloromethane (200 ml)
5. washwashed with hydrochloric acid (2N aqueous solution) (4×100 ml)
6. customThe organic layer was separated
7. washwashed with Na2CO3 (10% aqueous solution) (50 ml)
8. dry with materialdried over anhydrous MgSO4 (s)
9. filtrationfiltered
10. customevaporated in vacuo

ORD record

ord-66468c3f96664c8d8f80ba5024ed57c6

Source dataset

uspto-grants-2012_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08134007B2