Formic Acid → Formamide, N-(4-bromophenyl)-

HRID 2389587Notes

Reaction equation

HRID 2389587 reaction equation
[CH:1]([OH:3])=O.C(OC(=O)C)(=O)C.[Br:11][C:12]1[CH:18]=[CH:17][C:15]([NH2:16])=[CH:14][CH:13]=1>O>[Br:11][C:12]1[CH:18]=[CH:17][C:15]([NH:16][CH:1]=[O:3])=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 284Formic AcidHCID 78074-BromoanilineHCID 7918Acetic Anhydride

Product 1

HCID 17474Formamide, N-(4-bromophenyl)-

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A stirred solution of formic acid (2.5 mL, 88% in water) is cooled to 0° C., treated with acetic anhydride (0.82 mL, 9.0 mmol) then warmed to RT over 30 minutes. The solution is then cooled to 0° C. and 4-bromoaniline (500 mg, 3.0 mmol) added dropwise over 5 minutes. After stirring a further 16 h at RT, the reaction mixture is diluted with water (20 mL) and extracted into DCM (3×20 mL). The combined DCM phases are washed with 1 M HCl (20 mL) and aqueous NaHCO3 (20 mL), dried over Na2SO4 and reduced in vacuo. Purification by column chromatography (20% EtOAc in heptane) affords the title compound.

Workup

  1. temperatureThe solution is then cooled to 0° C.
  2. extractionextracted into DCM (3×20 mL)
  3. washThe combined DCM phases are washed with 1 M HCl (20 mL) and aqueous NaHCO3 (20 mL)
  4. dry with materialdried over Na2SO4
  5. customPurification by column chromatography (20% EtOAc in heptane)

Sources & evidence

ORD record
ord-fc4c40687e0843958e4764e9965ab065
Source dataset
uspto-grants-2012_09
Patent number
US08273747B2

Reaction notes

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