Potassium Carbonate → 7-Bromo-N,N-dimethyl-benzofuran-2-carboxamide

HRID 383813Notes

Reaction equation

HRID 383813 reaction equation
[Br:1][C:2]1[C:3]([OH:10])=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=O.Cl[CH2:12][C:13]([N:15]([CH3:17])[CH3:16])=[O:14].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[Br:1][C:2]1[C:3]2[O:10][C:12]([C:13]([N:15]([CH3:17])[CH3:16])=[O:14])=[CH:5][C:4]=2[CH:7]=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 758862-chloro-N,N-dimethylacetamideHCID 109105553-Bromo-2-hydroxybenzaldehyde

Product 1

HCID 403935587-Bromo-N,N-dimethyl-benzofuran-2-carboxamideYield 99.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 3-bromo-2-hydroxybenzaldehyde (5 g, 24.87 mmol), 2-chloro-N,N-dimethylacetamide (3.33 ml, 32.34 mmol) and potassium carbonate (6.88 g, 49.75 mmol) in DMF (60 ml) was heated at reflux for 1 h. The solids were filtered off and the filtrate was concentrated. The residue was taken up in ethyl acetate and washed with sat. NaCl(aq). The layers were separated and the aqueous layer was extracted with ethyl acetate (2×50 mL). The combined organic layer was dried with sodium sulfate, filtered and concentrated to give the title compound (6.63 g, 99%) as a crude product which was used as such in subsequent reaction.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 1 h
  3. filtrationThe solids were filtered off
  4. concentrationthe filtrate was concentrated
  5. washwashed with sat. NaCl(aq)
  6. customThe layers were separated
  7. extractionthe aqueous layer was extracted with ethyl acetate (2×50 mL)
  8. dry with materialThe combined organic layer was dried with sodium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-e66cb20df0e94cb68313574a9af33716
Source dataset
uspto-grants-2013_02
Patent number
US08367676B2

Reaction notes

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