Water → 2-[(2-Bromophenyl)thio]acetonitrile

Temperature

25 °C

A mixture of 2-bromobenzenethiol (6.3 mL, 53 mmol), K2CO3 (13.8 g, 100 mmol) and 2-chloroacetonitrile (3.2 mL, 50 mmol) in DMF (50 mL) was stirred at 25° C. for 6 h, poured into water (700 mL), and extracted with petroleum ether (300 mL) followed by DCM (2×200 mL). The combined DCM extracts were concentrated to dryness, and re-dissolved in petroleum ether/ethyl acetate (10:1, 600 mL). The organic solution was washed with water (250 mL) and brine (250 mL), dried over Na2SO4, filtered and concentrated to dryness to give the title compound (11 g, 85%). 1H NMR (300 MHz, CDCl3) δ 7.67 (dd, J=7.8, 1.5, 1H), 7.60 (dd, J=7.8, 1.5, 1H), 7.41 (m, 1H), 7.25 (m, 1H), 3.68 (s, 2H).

1. extractionextracted with petroleum ether (300 mL)
2. concentrationThe combined DCM extracts were concentrated to dryness
3. dissolutionre-dissolved in petroleum ether/ethyl acetate (10:1, 600 mL)
4. washThe organic solution was washed with water (250 mL) and brine (250 mL)
5. dry with materialdried over Na2SO4
6. filtrationfiltered
7. concentrationconcentrated to dryness

ORD record

ord-1c506a31a4b44e4e9f80e60f4267babd

Source dataset

uspto-grants-2015_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09079866B2