2(3H)-Benzoxazolone → 6-Bromo-2(3H)-benzoxazolone

HRID 2085750Notes

Reaction equation

HRID 2085750 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[NH:3][C:2]1=[O:10].[Br:11]N1C(C)(C)C(=O)N(Br)C1=O.FC(F)(F)S(O)(=O)=O>ClCCl>[Br:11][C:7]1[CH:8]=[CH:9][C:4]2[NH:3][C:2](=[O:10])[O:1][C:5]=2[CH:6]=1

Participants

5

Reactant 3

HCID 60432(3H)-BenzoxazoloneHCID 64791,3-Dibromo-5,5-dimethylhydantoinHCID 62406Trifluoromethanesulfonic acid

Product 1

HCID 298596-Bromo-2(3H)-benzoxazolone

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 2-benzoxazolinone (3.00 g, 22.2 mmol), 1,3-dibromo-5,5-dimethylhydantoin (3.49 g, 12.2 mmol), and trifluoromethanesulfonic acid (5.00 g, 33.3 mmol) in dichloromethane (100 mL) at room temperature was protected from light, stirred for 1 hour, and concentrated. The concentrate was purified by flash column chromatography on silica gel with 50% ethyl acetate/hexanes to provide the desired product.

Workup

  1. concentrationconcentrated
  2. customThe concentrate was purified by flash column chromatography on silica gel with 50% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-c8c83539ac9041f09121bd8aa279b65c
Source dataset
uspto-grants-2004_04
Patent number
US06720338B2

Reaction notes

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