Isobutyronitrile → 3-(2-Bromophenyl)-2,2-dimethylpropanenitrile

To a solution of isobutyronitrile (3.58 g, 52 mmol) in dry THF (30 mL) was added LiHMDS (1.0 M in THF) (80 mL, 80 mmol) at 0° C., stirred for 20 min, and to this solution was added 1-bromo-2-(bromomethyl)benzene (10 g, 40 mmol) in dry THF (70 mL). After 3 h at rt, the reaction mixture was quenched with saturated NH4Cl solution, extracted with EtOAc (2×), the combined organics were washed with H2O, brine, dried over Na2SO4, filtered and concentrated to give 9.5 g (99%) of Intermediate 24A as red wine liquid. 1H NMR (400 MHz, CDCl3) δ 7.57-7.60 (2H, m), 7.30-7.34 (1H, m), 7.12-7.17 (1H, m), 3.08 (2H, s), 1.4 (6H, s) ppm.

1. waitAfter 3 h at rt
2. customthe reaction mixture was quenched with saturated NH4Cl solution
3. extractionextracted with EtOAc (2×)
4. washthe combined organics were washed with H2O, brine
5. dry with materialdried over Na2SO4
6. filtrationfiltered
7. concentrationconcentrated

ORD record

ord-c0fcc3448fea4b16ac2dd1498b7973c6

Source dataset

uspto-grants-2016_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09447110B2