Dimethylformamide → 2-Bromo-N-(4-cyanophenyl)acetamide

Temperature

0 °C

A solution of 4-aminobenzonitrile (5.0 g, 42.3 mmol) in a mixture of anhydrous DMF (30 mL) and anhydrous dioxane (30 mL) in a 250 mL 3-necked round-bottomed flask equipped with a constant addition funnel (60 mL) was cooled to 0° C. using an ice-bath. Bromoacetyl bromide (8.53 g, 3.7 mL, 42.3 mmol) was added dropwise, keeping the internal temperature between 0° and 5° C. over a 1/2 h period. After the addition of the bromoacetyl bromide was completed, the solution was warmed to rt, stirred overnight, and then the solution was slowly poured into 500 mL of ice-water, causing a pale brown solid to precipitate. The precipitate was filtered, washed with water, and then dried in a vacuum dessicator overnight to afford 7.78 g (77%) of the title compound as a pale brown solid, mp 166°-168° C.: 1H NMR (DMSO-d6) δ10.81 (s, 1H), 7.81-7.74 (m, 4H), 4.08 (s, 2H); 13C NMR (DMSO-d6) δ165.60, 142.75, 133.39, 119.28, 118.89, 105.60, 30.17; MS (EI, m/z) 238 (M+).

1. customequipped with a constant addition funnel (60 mL)
2. customthe internal temperature between 0° and 5° C.
3. customover a 1/2 h
4. temperaturethe solution was warmed to rt
5. customto precipitate
6. filtrationThe precipitate was filtered
7. washwashed with water
8. customdried in a vacuum dessicator overnight

ORD record

ord-7d6947d498294b36841b68ea0f600519

Source dataset

uspto-grants-1998_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05741926