Water → 6-Bromo-2(3H)-benzoxazolone

HRID 478900Notes

Reaction equation

HRID 478900 reaction equation
[CH:1]1[CH:2]=[CH:3][C:4]2[O:10][C:8](=[O:9])[NH:7][C:5]=2[CH:6]=1.[Br:11]N1C(=O)CCC1=O.O>C(O)(=O)C>[Br:11][C:2]1[CH:1]=[CH:6][C:5]2[NH:7][C:8](=[O:9])[O:10][C:4]=2[CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 60432(3H)-BenzoxazoloneHCID 67184N-bromobutanimide

Product 1

HCID 298596-Bromo-2(3H)-benzoxazoloneYield 79.2%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of benzoxazolinone (20 g, 0.148 mol) in 220 mL glacial acetic acid was added N-bromosuccinimide (NBS, 26.36 g, 0.148 mol), and the reaction mixture was stirred at room temperature for 63 hours before pouring into 1500 mL water. The precipitated product was washed thoroughly with water upon collection and recrystallized from EtOH to give 6-bromo-3H-benzoxazol-2-one (9) (25.09 g, 79%): Theory: C, 39.28; H, 1.88; N, 6.54; Br, 37.33. Found: C, 39.36; H, 2.02; N, 6.36; Br, 37.43. MP 192-194° C.

Workup

  1. washThe precipitated product was washed thoroughly with water upon collection
  2. customrecrystallized from EtOH

Sources & evidence

ORD record
ord-dac3782455a24e4eb57d58ee0efa29ce
Source dataset
uspto-grants-2003_11
Patent number
US06642256B2

Reaction notes

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