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

HRID 842333Notes

Reaction equation

HRID 842333 reaction equation
C([O-])(=O)C.[Na+].[O:6]1[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[NH:8][C:7]1=[O:15].[Br:16]Br>C(O)(=O)C>[Br:16][C:12]1[CH:13]=[CH:14][C:9]2[NH:8][C:7](=[O:15])[O:6][C:10]=2[CH:11]=1

Participants

5

Reactant 3

HCID 60432(3H)-BenzoxazoloneHCID 24408BromineHCID 517045Sodium Acetate

Product 1

HCID 298596-Bromo-2(3H)-benzoxazoloneYield 89.7%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of glacial acetic acid (1500 ml) was added sodium acetate (222 g, 2.70 mole) and 2-benzoxazolinone (300 g, 2.22 mole). The suspension was cooled to 15° C. bromine (118 ml, 2.29 mole) added dropwise over 1 h and the mixture stirred for 12 h at ambient temperature. The solids were then filtered, washed with H2O (3×500 ml) and dried under vacuum to give the title compound as a white solid (374 g, 89.7%): mp 186.0-187.0° C.: 1H NMR (DMSO-d6) δ 11.8 (s, 1 H), 7.6 (s, 1 H), 7.3 (d, J=8.0 Hz, 1 H), 7.0 (d, J=8.0 Hz, 1 H).

Workup

  1. additionadded dropwise over 1 h
  2. filtrationThe solids were then filtered
  3. washwashed with H2O (3×500 ml)
  4. customdried under vacuum

Sources & evidence

ORD record
ord-4ee452af77634a4c890790a1d2022e10
Source dataset
uspto-grants-2002_04
Patent number
US06372933B1

Reaction notes

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