Bromine → Bromo(4-chlorophenyl)acetonitrile

Temperature

25 °C

4-Chlorophenylacetonitrile (303.2 g., 2.0 mole) is heated to 90°C. on a steam bath and 48% hydrobromic acid (5drops) is added. Bromine (336 g., 2.1 mole) is then added dropwise to the stirred melt over a 1-hour period at 90° -95°C. The reaction mixture is heated an additional 15 minutes and then cooled. Benzene (300 ml.) is then added and 100 ml. of the benzene is removed by distillation at 80°C. The solution is cooled, filtered and the benzene removed to afford 435.5 g. of crude product which is extracted with 3 liters of hexane at 50°-55°C. Isopropanol (100 ml.) is added to the hexane solution which is then cooled to 25°C. The product is collected by filtration to afford 235.2 g. (57% yield) of 4-chlorophenyl-α-bromoacetonitrile, m.p. 46°-49°C.

1. temperatureThe reaction mixture is heated an additional 15 minutes
2. temperaturecooled
3. customof the benzene is removed by distillation at 80°C
4. temperatureThe solution is cooled
5. filtrationfiltered
6. customthe benzene removed
7. customto afford 435.5 g
8. extractionof crude product which is extracted with 3 liters of hexane at 50°-55°C
9. additionIsopropanol (100 ml.) is added to the hexane solution which
10. filtrationThe product is collected by filtration
11. customto afford 235.2 g

ORD record

ord-d9a544e858fe492087ac731217b12863

Source dataset

uspto-grants-1976_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US03953490