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

HRID 383854

반응식

HRID 383854 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

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%).

후처리

  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%)

출처 및 근거

ORD 기록
ord-69fe797349ed4674b4e48f6986d20ef4
출처 데이터셋
uspto-grants-2013_02
특허 번호
US08367676B2

연결된 노트

불러오는 중…