Dimethylformamide → 2-(4-Bromo-2-trifluoromethyl-phenyl)2-methyl-propionitrile

NaH 95% (2.28 g, 94.7 mmol) was suspended in DMF (25 mL) and cooled to 0° C. (4-Bromo-2-trifluoromethyl-phenyl)-acetonitrile (5 g, 18.94 mmol) from step 2 above, was dissolved in THF (35 mL) and slowly added via cannula to the NaH suspension. The reaction mixture was stirred for 20 min. Methyl iodide (11.79 mL, 189.36 mmol) was added and the resulting mixture was stirred overnight at room temperature. Reaction was quenched with H2O (100 mL). Solvents were removed in vacuo and residue partitioned between EtOAc and 1N HCl (100 mL). The organic phase was dried over Na2SO4 and evaporated. The crude organic product was purified by flash column chromatography (5% EtOAc in hexanes) to give the product (4.14 g, 75%) as a clear oil. 1H NMR (400 MHz, CDCl3) δ 1.6 (s, 6H), 7.46 (d, J=8.3 Hz, 1H), 7.67 (d, J=8.3 Hz, 1H), 7.78 (s, 1H).

1. stirringthe resulting mixture was stirred overnight at room temperature
2. customReaction
3. customwas quenched with H2O (100 mL)
4. customSolvents were removed in vacuo and residue
5. custompartitioned between EtOAc and 1N HCl (100 mL)
6. dry with materialThe organic phase was dried over Na2SO4
7. customevaporated
8. customThe crude organic product was purified by flash column chromatography (5% EtOAc in hexanes)

ORD record

ord-cdff679f8f5a4b4aa503a8b247ebb478

Source dataset

uspto-grants-2009_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07622605B2