Sodium Thiosulfate → 4-Bromo-2-(2,2,2-trifluoroethyl)phenol

Tetrabutylammonium tribromide (6.56 g) was dissolved in chloroform (50 ml) and added dropwise to a solution of 2-(2,2,2-trifluoroethyl)phenol (2.4 g) in chloroform (50 ml). The reaction mixture was stirred at room temperature for 2 hrs, after which time 5% sodium thiosulfate solution (100 ml) was added and the resultant stirred for 30 mins. The mixture was then partitioned between dichloromethane (100 ml) and 1N HCl (200 ml). The organics were separated and dried over magnesium sulfate. The solvent was then removed in vacuo, the crude residue was then purified by column chromatography on silica gel eluting with 90:10 hexanes:ethyl acetate to afford the title compound as a yellow oil (3.24 g). 1H NMR (CDCl3): δ 3.50 (q, J=21.48 Hz 2H), 6.70 (d, J=2.54 Hz, 1H), 7.32 (d, J=2.54 Hz, 1H), 7.45 (s, 1H).

1. stirringthe resultant stirred for 30 mins
2. customThe mixture was then partitioned between dichloromethane (100 ml) and 1N HCl (200 ml)
3. customThe organics were separated
4. dry with materialdried over magnesium sulfate
5. customThe solvent was then removed in vacuo
6. customthe crude residue was then purified by column chromatography on silica gel eluting with 90:10 hexanes

ORD record

ord-a74ed0a64a4b4f1c8a1e76182397f985

Source dataset

uspto-grants-2012_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08268835B2