Ammonium Hydroxide → 4-Bromo-2-fluorobenzamide

HRID 1020937Notes

Reaction equation

HRID 1020937 reaction equation
C(N1C=CN=C1)([N:3]1C=CN=C1)=O.[Br:13][C:14]1[CH:22]=[CH:21][C:17]([C:18](O)=[O:19])=[C:16]([F:23])[CH:15]=1.[OH-].[NH4+]>ClCCl>[Br:13][C:14]1[CH:22]=[CH:21][C:17]([C:18]([NH2:3])=[O:19])=[C:16]([F:23])[CH:15]=1

Participants

5

Reactant 3

HCID 14923Ammonium HydroxideHCID 682631,1'-CarbonyldiimidazoleHCID 3026814-Bromo-2-fluorobenzoic acid

Product 1

HCID 27733314-Bromo-2-fluorobenzamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

At 0° C., 1,1′-carbonyldiimidazole (8.8 g, 54.3 mmol) was added in portions to a stirred mixture of 4-bromo-2-fluorobenzoic acid (6 g, 27.3 mmol) in dichloromethane (100 ml). After 20 minutes, a clear solution was obtained. Ammonium hydroxide (28%, 30 ml) was added and the mixture was stirred overnight. Aqueous layer was isolated, extracted with dichloromethane twice. Combined organic extracts were washed with water, 1 N HCl twice, water, brine and dried (MgSO4). Solvent was removed under vacuum, and the solid was washed with hexane to afford 4-bromo-2-fluoro-benzamide 2BL (5.56 g).

Workup

  1. customa clear solution was obtained
  2. customAqueous layer was isolated
  3. extractionextracted with dichloromethane twice
  4. washCombined organic extracts were washed with water, 1 N HCl twice
  5. dry with materialwater, brine and dried (MgSO4)
  6. customSolvent was removed under vacuum
  7. washthe solid was washed with hexane

Sources & evidence

ORD record
ord-a4001f22ef5c409d91562f2bb7bb0339
Source dataset
uspto-grants-2014_05
Patent number
US08716483B2

Reaction notes

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