Water → 4-Bromo-1,2-benzoxazol-3-amine

HRID 239879Notes

Reaction equation

HRID 239879 reaction equation
CC(C)([O-])C.[K+].[Br:7][C:8]1[CH:15]=[CH:14][CH:13]=[C:12](F)[C:9]=1[C:10]#[N:11].[OH2:17].C[N:19](C=O)C>>[Br:7][C:8]1[C:9]2[C:10]([NH2:19])=[N:11][O:17][C:12]=2[CH:13]=[CH:14][CH:15]=1

Participants

5

Reactant 4

HCID 962WaterHCID 6228DimethylformamideHCID 27831392-Bromo-6-fluorobenzonitrileHCID 23665647Potassium tert-butoxide

Product 1

HCID 455884714-Bromo-1,2-benzoxazol-3-amine

Procedure

A suspension of acetylhydroxamic acid (2.46 g, 32.8 mmol) and potassium tert-butoxide (3.68 g, 32.8 mmol) in DMF (40 mL) was stirred at room temperature for 30 minutes, treated with 2-bromo-6-fluorobenzonitrile (4.36 g, 21.8 mmol), stirred for three hours, poured into water, and extracted three times with ethyl acetate. The combined extracts were washed with brine, dried (MgSO4), filtered, and concentrated. The residue was purified by flash column chromatography on silica gel with 5 to 20% ethyl acetate/hexanes to provide 2.5 g of the desired product. MS (ESI(+)) m/e 212.9, 214.9 (M+H)+.

Workup

  1. stirringstirred for three hours
  2. extractionextracted three times with ethyl acetate
  3. washThe combined extracts were washed with brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by flash column chromatography on silica gel with 5 to 20% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-2877c95eafc344d49b3094d755c12753
Source dataset
uspto-grants-2014_02
Patent number
US08642776B2

Reaction notes

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