Reaction #5334

Reaction equation

4'-methylbiphenyl-2-carboxamide

N-bromo-succinimide

AIBN

→

4'-bromomethylbiphenyl-2-carboxamide

Solvents

benzene

Conditions

Workup

1. 1
   OtherResulting crystalline precipitates
2. 2
   Filtrationwere collected by filtration
3. 3
   Washwashed with isopropylether
4. 4
   workup.STIRRINGThe suspension was stirred for 30 minutes
5. 5
   Filtrationinsoluble materials were collected by filtration
6. 6
   Otherdried
7. 7
   Otherto give crude crystals
8. 8
   OtherRecrystallization from ethyl acetate methanol afforded colorless needles (1.6 g, 55%), m.p. 220°-221° C. (decomp.)

Procedure

A mixture of 4'-methylbiphenyl-2-carboxamide (2.1 g), N-bromo-succinimide (2.5 g) and azobisisobutyronitrate (AIBN; 82 mg) in benzene (20 ml) was stirred for 20 hours at 60° to 70° C. Resulting crystalline precipitates were collected by filtration, washed with isopropylether and suspended in water. The suspension was stirred for 30 minutes, and insoluble materials were collected by filtration and dried to give crude crystals. Recrystallization from ethyl acetate methanol afforded colorless needles (1.6 g, 55%), m.p. 220°-221° C. (decomp.).

Source