Reaction #7810

Reaction equation

2-[3-(methoxymethoxy)-4-methylphenyl]-1,3-benzoxazole

NBS

benzoyl peroxide

→

2-[4-(bromomethyl)-3-(methoxymethoxy)phenyl]-1,3-benzoxazole

Solvents

CCl4

Conditions

Workup

1. 1
   OtherCCl4 was removed in vacuo and residue
2. 2
   Otherwas purified by flash column (silica gel, hexanes:EtOAc 5:1)

Procedure

A solution of 2-[3-(methoxymethoxy)-4-methylphenyl]-1,3-benzoxazole (200 mg, 0.74 mmol, 84%), NBS (179 mg, 0.81 mmol), and benzoyl peroxide (50 mg) in CCl4 (10 mL), was refluxed for 12 h. After cooling to rt, CCl4 was removed in vacuo and residue was purified by flash column (silica gel, hexanes:EtOAc 5:1) to afford 2-[4-(bromomethyl)-3-(methoxymethoxy)phenyl]-1,3-benzoxazole. MS (ESI) 349 (M+H)+.

Source