Reaction #7806

Reaction equation

2-(3-{[tert-butyl-(dimethyl)silyl]oxy}-4-methylphenyl)-1,3-benzoxazole

NBS

benzoyl peroxide

→

2-(3-{[tert-butyl-(dimethyl)silyl]oxy}-4-bromomethylphenyl)-1,3-benzoxazole

Solvents

CCl4

Conditions

Workup

1. 1
   TemperatureThe reaction mixture was refluxed for 6 h
2. 2
   OtherCCl4 was removed in vacuo
3. 3
   workup.DISSOLUTIONThe residue was dissolved in EtOAc (50 mL)
4. 4
   Washwashed with H2O (50 mL)
5. 5
   Dryingdried (MgSO4)
6. 6
   Filtrationfiltered
7. 7
   Concentrationconcentrated in vacuo

Procedure

To 2-(3-{[tert-butyl-(dimethyl)silyl]oxy}-4-methylphenyl)-1,3-benzoxazole (1.46 g, 4.3 mmol) in CCl4 (50 mL) was added NBS (770 mg, 4.3 mmol) and benzoyl peroxide (50 mg). The reaction mixture was refluxed for 6 h, cooled to rt, and CCl4 was removed in vacuo. The residue was dissolved in EtOAc (50 mL), washed with H2O (50 mL), dried (MgSO4), filtered and concentrated in vacuo to afford 2-(3-{[tert-butyl-(dimethyl)silyl]oxy}-4-bromomethylphenyl)-1,3-benzoxazole as light yellow solid.

Source