Dimethylformamide → 2-(4-Bromo-2-chlorophenyl)-2-methylpropanenitrile

Temperature

0 °C

NaH (95%, 1.18 g, 49.35 mmol) was suspended in DMF (25 mL) and cooled to 0° C. 4-bromo-2-chloro-phenyl)-acetonitrile (2.27 g, 9.87 mmol) from step 3 above, was dissolved in THF (10 mL) and slowly added via cannula and the reaction mixture stirred 20 min. MeI (6.10 mL, 98 mmol) was added and the resulting mixture was stirred overnight at room temperature. Reaction was quenched with H2O (50 mL). Solvents were removed in vacuo and residue partitioned between EtOAc and 1N HCl (50 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 (2.23 g, 87%) as a clear oil. 1H NMR (400 MHz, CDCl3): δ 7.34 (d, J=8.4 Hz, 1H), 7.43 (dd, J=8.4, 2.0 Hz, 1H), 7.61 (d, J=1.8 Hz, 1H).

1. additionslowly added via cannula
2. stirringthe resulting mixture was stirred overnight at room temperature
3. customReaction
4. customwas quenched with H2O (50 mL)
5. customSolvents were removed in vacuo and residue
6. custompartitioned between EtOAc and 1N HCl (50 mL)
7. dry with materialThe organic phase was dried over Na2SO4
8. customevaporated
9. customThe crude organic product was purified by flash column chromatography (5% EtOAc in hexanes)

ORD record

ord-7ea720a1170e4700adb5ca15226da4ff

Source dataset

uspto-grants-2012_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08268835B2