Water → (4-Bromo-3-(trifluoromethoxy)phenyl)methanol

Temperature

0 °C

To a cooled and stirred solution of methyl 4-bromo-3-(trifluoromethoxy)benzoate (28.2, 2.60 g, 8.70 mmol) in THF (20 mL) under nitrogen, was added DIBAL-H (19.2 mL, 1.0 M in toluene) at −78° C. The reaction mixture was stirred at 0° C. for 10 minutes and 5.0 mL of water was added. The resulting mixture was stirred at room temperature for 2 hours. The solid was then filtered off. EtOAc (100 mL) was added, and the mixture was washed with brine (20 mL) and dried with Na2SO4. The solvent was removed to give 28.3. 1H NMR (CDCl3) δ 1.91 (s, 1H), 4.71 (s, 2 H), 7.18 (d, J=6.3 Hz, 1H), 7.36 (s, 1H), 7.63 (d, J=6.3 Hz, 1 H).

1. temperatureTo a cooled
2. stirringThe resulting mixture was stirred at room temperature for 2 hours
3. filtrationThe solid was then filtered off
4. additionEtOAc (100 mL) was added
5. washthe mixture was washed with brine (20 mL)
6. dry with materialdried with Na2SO4
7. customThe solvent was removed

ORD record

ord-8d6f73bcdf0c4e71b1fa9720be8e71f6

Source dataset

uspto-grants-2011_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08003648B2