Reaction #7786

Reaction equation

5′-(1,3-benzoxazol-2-yl)-2′-methyl-1,1′-biphenyl-3-carbonitrile

n-bromosuccinimide

benzoyl peroxide

→

5′-(1,3-benzoxazol-2-yl)-2′-(bromomethyl)-1,1′-biphenyl-3-carbonitrile

Solvents

carbon tetrachloride

Conditions

Workup

1. 1
   Temperaturewas refluxed for 5 h
2. 2
   OtherThe solvent was evaporated to dryness
3. 3
   Otherthe crude was purified by flash chromatography on silica gel eluting with a gradient of EtOAc

Procedure

A mixture of 5′-(1,3-benzoxazol-2-yl)-2′-methyl-1,1′-biphenyl-3-carbonitrile (229 mg, 0.74 mmol), n-bromosuccinimide (145 mg, 0.81 mmol), and benzoyl peroxide (9 mg, 0.037 mmol) in carbon tetrachloride (15 mL) was refluxed for 5 h. The solvent was evaporated to dryness and the crude was purified by flash chromatography on silica gel eluting with a gradient of EtOAc:hexanes (0 to 30 min: 0 to 20% EtOAc, 30 to 40 min: 50% EtOAc) to afford 5′-(1,3-benzoxazol-2-yl)-2′-(bromomethyl)-1,1′-biphenyl-3-carbonitrile as a colorless solid.

Source