Reaction #6021

Reaction equation

product

Methyl 2-(4-methylphenoxy)-2-(2'-chlorophenyl)acetate

N-bromosuccinimide

AIBN

→

Methyl 2-(4-bromomethylphenoxy)-2-(2'-chlorophenyl)acetate

Yield 73.0%

Solvents

CCl4

Conditions

Workup

1. 1
   ConcentrationThe reaction mixture was concentrated in vacuo
2. 2
   Otherchromatographed on silica gel (125×20 mm)
3. 3
   Washeluting with 5% ethyl acetate in hexane
4. 4
   OtherThe product was isolated in a 73% yield (186 mg)

Procedure

A solution of the product of Example 3, Step B (0.2 g, 0.69 mmol), N-bromosuccinimide (117 mg, 166 mmol) and a catalytic amount of AIBN in 2 ml CCl4 was refluxed for 30 minutes. The reaction mixture was concentrated in vacuo and chromatographed on silica gel (125×20 mm) eluting with 5% ethyl acetate in hexane. The product was isolated in a 73% yield (186 mg).

Source