Benzoyl Peroxide → 2-(Bromomethyl)-5-chlorobenzo[d]oxazole

HRID 1032322

Reaction equation

HRID 1032322 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][C:8]([CH3:10])=[N:7][C:6]=2[CH:11]=1.[Br:12]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][C:8]([CH2:10][Br:12])=[N:7][C:6]=2[CH:11]=1

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 295105-Chloro-2-methylbenzoxazoleHCID 67184N-bromobutanimide

Product 1

HCID 127459452-(Bromomethyl)-5-chlorobenzo[d]oxazole

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A solution of the benzoxazole (1.3 g) (Step 2) in CCl4 (15 mL) was treated with N-bromo-succinimide (NBS) (1.5 g) and benzoyl peroxide (38 mg) at reflux using a U.V. lamp for 24 hours. Filtration, evaporation, and flash chromatography of the residue using 1:1 hexane/toluene afforded the title compound which was used as such for the next step.

Workup

  1. temperatureat reflux
  2. filtrationFiltration, evaporation, and flash chromatography of the residue

Sources & evidence

ORD record
ord-c8a92444ed334775971a2479e214d719
Source dataset
uspto-grants-1990_09
Patent number
US04957932

Linked notes

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