2(3H)-Benzoxazolone → 5-(2-Bromopropanoyl)-1,3-benzoxazol-2(3H)-one

HRID 1731322Notes

Reaction equation

HRID 1731322 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[Br:5][CH:6]([CH3:10])[C:7](Br)=[O:8].[O:11]1[C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=2[NH:13][C:12]1=[O:20]>C(=S)=S>[Br:5][CH:6]([CH3:10])[C:7]([C:18]1[CH:17]=[CH:16][C:15]2[O:11][C:12](=[O:20])[NH:13][C:14]=2[CH:19]=1)=[O:8]

Participants

5

Reactant 3

HCID 60432(3H)-BenzoxazoloneHCID 79047Propanoyl bromide, 2-bromo-HCID 6451240Aluminum(III) Chloride

Product 1

HCID 139361585-(2-Bromopropanoyl)-1,3-benzoxazol-2(3H)-oneYield 50%

Reagents, catalysts & solvents 1

HCID 6348Carbon DisulfideSolvent

Procedure

A mixture of aluminum chloride (40 g) and 2-bromopropionyl bromide (32.4 g) in carbon disulfide (100 ml) was refluxed with stirring for 30 minutes. To the resultant mixture was added 2-benzoxazolinone (13.5 g) and the mixture was refluxed under stirring for 7 hours. The reaction mixture was poured into ice-water and extracted with ethyl acetate. The extract was washed with brine and dried over magnesium sulfate. The solvent was evaporated in vacuo to afford a crystalline residue, which was recrystallized from a mixture of ethyl acetate and diethyl ether to give 5-(2-bromopropionyl)-2-benzoxazolinone (13.5 g). mp. 191°-193° C.

Workup

  1. temperaturewas refluxed
  2. temperaturethe mixture was refluxed
  3. stirringunder stirring for 7 hours
  4. extractionextracted with ethyl acetate
  5. washThe extract was washed with brine
  6. dry with materialdried over magnesium sulfate
  7. customThe solvent was evaporated in vacuo
  8. customto afford a crystalline residue, which
  9. customwas recrystallized from a mixture of ethyl acetate and diethyl ether

Sources & evidence

ORD record
ord-43e94d772bf1493e9e086125c1f97099
Source dataset
uspto-grants-1986_11
Patent number
US04621084

Reaction notes

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