Isopropanol → 5-Bromo-2-isopropoxybenzotrifluoride

Temperature

50 °C

To a solution of 2-propanol (1.997 mL) in dry tetrahydrofuran (THF) (50 mL) under nitrogen was added potassium tert-butoxide (3.49 g). The reaction mixture was heated to 50° C. for 10 min, then 4-bromo-1-fluoro-2-(trifluoromethyl)benzene (D40) (6.3 g) was added. The resulting mixture was stirred at 50° C. overnight. After cooling the reaction, the solvent was removed in vacuo, the residue was diluted with ethyl acetate (100 mL), washed with water, the organic phase was dried over sodium sulphate, concentrated and the residue was purified by column chromatography to give 4-bromo-1-[(1-methylethyl)oxy]-2-(trifluoromethyl)benzene (D41) (5.21 g) as a clear oil. δH (CDCl3, 600 MHz): 1.36 (6H, d), 4.60 (1H, m), 6.88 (1H, d), 7.55 (1H, dd), 7.66 (1H, d).

1. temperatureAfter cooling
2. customthe reaction
3. customthe solvent was removed in vacuo
4. additionthe residue was diluted with ethyl acetate (100 mL)
5. washwashed with water
6. dry with materialthe organic phase was dried over sodium sulphate
7. concentrationconcentrated
8. customthe residue was purified by column chromatography

ORD record

ord-728d545d403342b3b9f0bd3c9f63866d

Source dataset

uspto-grants-2013_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08389508B2