Boron tribromide → m-(Trifluoromethyl)benzamide

To a solution of (R)-4-fluoro-N-(1-(4-fluoro-3-methoxyphenyl)-1-(3-fluoro-5-(1,1,2,2-tetrafluoroethoxy)phenyl)-2-phenylethyl)-3-(trifluoromethyl)benzamide, prepared as described in Procedure 3, 59a-f, 6 and 7, (2.8 g, 4.43 mmol) in CH2Cl2 (15 mL) was added BBr3 (12 mL, 12 mmol). The resulting mixture was stirred at room temperature for 2 h and quenched by addition of ice. The reaction mixture was diluted with EtOAc and washed with sat. NaHCO3, sat. NaCl, dried over Na2SO4, filtered and concentrated to afford (R)-4-fluoro-N-(1-(4-fluoro-3-hydroxyphenyl)-1-(3-fluoro-5-(1,1,2,2)-tetrafluoro ethoxy)phenyl)-2-phenylethyl)-3-(trifluoromethyl)benzamide (Example 264) as clear oil (2.9 g, 100% yield). LCMS: RT=4.176 min [M+H] 632.2 (4 min Phenomenex Luna C18 column, 4.6×50 mm eluting with 10-90% MeOH/H2O over 4 minutes containing 0.1% TFA; 4 mL/min, monitoring at 220 nm).

1. customquenched by addition of ice
2. additionThe reaction mixture was diluted with EtOAc
3. washwashed with sat. NaHCO3, sat. NaCl
4. dry with materialdried over Na2SO4
5. filtrationfiltered
6. concentrationconcentrated

ORD record

ord-90c0e7c4672343a0981cc5f511961c43

Source dataset

uspto-grants-2014_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08642576B2