Sodium Cyanide → 2-(4-Bromo-2-methylphenyl)acetonitrile

4-Bromo-1-chloromethyl-2-methyl-benzene (63 g, 287 mmol) was dissolved in DMF (180 mL). NaCN (15.5 g, 316 mmol, 1.1 eq.) was added in 1 portion, and the reaction was stirred at room temperature overnight under a N2 atmosphere. The mixture was concentrated under reduced pressure, and the residue was taken into a mixture of sat. aq. NH4Cl (300 mL) and EtOAc (300 mL). The bi-phase solution was diluted with H2O (200 mL). The EtOAc layer was separated, and the aqueous layer was re-extracted with EtOAc (2×200 mL). The combined organic layers were washed with brine (3×300 mL), dried (Na2SO4), filtered, and concentrated under reduced pressure, yielding the title compound (58.8 g, 280 mmol, 98%) with acceptable purity as a brown oil, which solidified to a brown solid on standing. 1H-NMR (CDCl3, 300 MHz) δ ppm 2.34 (s, 3H); 3.63 (s, 2H); 7.26 (t, 1H); 7.38 (d, 2H).

1. concentrationThe mixture was concentrated under reduced pressure
2. additionthe residue was taken into a mixture of sat. aq. NH4Cl (300 mL) and EtOAc (300 mL)
3. additionThe bi-phase solution was diluted with H2O (200 mL)
4. customThe EtOAc layer was separated
5. extractionthe aqueous layer was re-extracted with EtOAc (2×200 mL)
6. washThe combined organic layers were washed with brine (3×300 mL)
7. dry with materialdried (Na2SO4)
8. filtrationfiltered
9. concentrationconcentrated under reduced pressure

ORD record

ord-c70531bebcb44fb4a0a5c11efdec709b

Source dataset

uspto-grants-2014_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08853258B2