6-Bromo-2(3H)-benzoxazolone → 2-Oxo-2,3-dihydro-1,3-benzoxazole-6-carbonitrile

HRID 1710649Notes

Reaction equation

HRID 1710649 reaction equation
Br[C:2]1[CH:11]=[CH:10][C:5]2[NH:6][C:7](=[O:9])[O:8][C:4]=2[CH:3]=1.[Cu](C#N)[C:13]#[N:14]>CN(C=O)C.C(OCC)(=O)C>[O:9]=[C:7]1[NH:6][C:5]2[CH:10]=[CH:11][C:2]([C:13]#[N:14])=[CH:3][C:4]=2[O:8]1

Participants

5

Reactant 2

HCID 298596-Bromo-2(3H)-benzoxazoloneHCID 178418260HCID 178418260, compound

Product 1

HCID 101762552-Oxo-2,3-dihydro-1,3-benzoxazole-6-carbonitrile

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 6-bromo-3H-benzooxazol-2-one (47) (400 mg, 1.87 mmol, 1 eq), copper cyanide (3.3 g, 37 mmol, 20 eq), in DMF (10 ml) was stirred at 175° C. for 3 hours. The reaction mixture was diluted with ethyl acetate, filtered to remove the precipitated solid material, and the organic phase was washed with water, purified by flash chromatography to give 2-oxo-2,3-dihydro-benzooxazole-6-carbonitrile (48).

Workup

  1. filtrationfiltered
  2. customto remove the precipitated solid material
  3. washthe organic phase was washed with water
  4. custompurified by flash chromatography

Sources & evidence

ORD record
ord-7f7708401b8d496698270d540779fca6
Source dataset
uspto-grants-2010_09
Patent number
US07790726B2

Reaction notes

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