Potassium Carbonate → 7-Bromo-5-methoxy-N,N-dimethylbenzofuran-2-carboxamide

HRID 383854

Reaction equation

HRID 383854 reaction equation
[Br:1][C:2]1[C:3]([OH:12])=[C:4]([CH:7]=[C:8]([O:10][CH3:11])[CH:9]=1)[CH:5]=O.Cl[CH2:14][C:15]([N:17]([CH3:19])[CH3:18])=[O:16].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[Br:1][C:2]1[C:3]2[O:12][C:14]([C:15]([N:17]([CH3:19])[CH3:18])=[O:16])=[CH:5][C:4]=2[CH:7]=[C:8]([O:10][CH3:11])[CH:9]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 758862-chloro-N,N-dimethylacetamideHCID 7358183-Bromo-2-hydroxy-5-methoxybenzaldehyde

Product 1

HCID 596367447-Bromo-5-methoxy-N,N-dimethylbenzofuran-2-carboxamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3-Bromo-2-hydroxy-5-methoxybenzaldehyde (1.5 g, 6.49 mmol), 2-chloro-N,N-dimethylacetamide (0.73 mL, 7.14 mmol) and potassium carbonate (1.8 g, 13.0 mmol) were heated to reflux in dimethylformamide (15 mL) for 2 h. The solvent was removed in vacuo and the residue was taken up in ethyl acetate and washed with water and brine. The organic phase was dried over MgSO4, filtered and then concentrated by rotary evaporation. The crude product was purified by flash chromatography (SiO2; heptane/EtOAc, gradient 0-100%). Yield: 1.5 g (77%).

Workup

  1. customThe solvent was removed in vacuo
  2. washwashed with water and brine
  3. dry with materialThe organic phase was dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated by rotary evaporation
  6. customThe crude product was purified by flash chromatography (SiO2; heptane/EtOAc, gradient 0-100%)

Sources & evidence

ORD record
ord-69fe797349ed4674b4e48f6986d20ef4
Source dataset
uspto-grants-2013_02
Patent number
US08367676B2

Linked notes

Loading…