Formic Acid → 4-Bromo-2-formylphenylformamide

HRID 566141Notes

Reaction equation

HRID 566141 reaction equation
[C:1](OC(=O)C)(=[O:3])C.C(O)=O.[NH2:11][C:12]1[CH:19]=[CH:18][C:17]([Br:20])=[CH:16][C:13]=1[CH:14]=[O:15].C(OC=O)=O>C1COCC1>[Br:20][C:17]1[CH:18]=[CH:19][C:12]([NH:11][CH:1]=[O:3])=[C:13]([CH:14]=[O:15])[CH:16]=1

Participants

6

Reactant 4

HCID 284Formic AcidHCID 7918Acetic AnhydrideHCID 9548680Formic anhydrideHCID 235104752-Amino-5-bromobenzaldehyde

Product 1

HCID 570527524-Bromo-2-formylphenylformamideYield 82%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Conditions

Temperature
60 °C

Procedure

To acetic acid anhydride (34.8 ml) was added formic acid (17.0 ml) at 0° C., and the mixture was stirred at 60° C. for 2 hours, cooled and diluted with THF (200 ml). In THF (100 ml) was dissolved 2-amino-5-bromobenzaldehyde (16.40 g), and the mixture was added dropwise to the previously prepared solution of formic acid anhydride in THF at 0° C. The mixture was stirred at 0° C. for 2 hours, and the solvent was evaporated under reduced pressure. The residue was washed with hexane and filtered to give 4-bromo-2-formylphenylformamide (15.24 g, 82%).

Workup

  1. temperaturecooled
  2. stirringThe mixture was stirred at 0° C. for 2 hours
  3. customthe solvent was evaporated under reduced pressure
  4. washThe residue was washed with hexane
  5. filtrationfiltered

Sources & evidence

ORD record
ord-0d0daed48eb94582b907969c25da363e
Source dataset
uspto-grants-2001_01
Patent number
US06172061B2

Reaction notes

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