Potassium Carbonate → Methyl 7-bromo-5-methoxybenzofuran-2-carboxylate

HRID 11150

반응식

HRID 11150 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.Br[CH:14](C(OC)=O)[C:15]([O:17][CH3:18])=[O:16].C(=O)([O-])[O-].[K+].[K+]>C1(C)C=CC=CC=1.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC>[Br:1][C:2]1[C:3]2[O:12][C:14]([C:15]([O:17][CH3:18])=[O:16])=[CH:5][C:4]=2[CH:7]=[C:8]([O:10][CH3:11])[CH:9]=1

참가 물질

6

반응물 3

HCID 11430Potassium CarbonateHCID 70087Dimethyl bromomalonateHCID 7358183-Bromo-2-hydroxy-5-methoxybenzaldehyde

생성물 1

HCID 21980481Methyl 7-bromo-5-methoxybenzofuran-2-carboxylate수율 56%

시약·촉매·용매 2

HCID 74236Tetrabutylammonium Bromide촉매HCID 1140Toluene용매

실험 절차

To a solution containing 3-Bromo-2-hydroxy-5-methoxy-benzaldehyde (94.7 g, 0.410 mol) and dimethyl bromomalonate (103 g, 0.492 mol) in toluene (1.2 L) was added freshly powdered potassium carbonate (85 g, 0.615 mol) and tetra-n-butylammonium bromide (13.2 g, 0.041 mol). The reaction was heated at reflux under a Dean-Stark trap for 48 h. The reaction was concentrated and the residue dissolved with dichloromethane (−0.5 L) and filtered through Celite, washing with dichloromethane (˜0.5 L). The filtrate was washed with 1 L of 1M sodium hydroxide and water (2×1 L). The organic phase was then passed through a 400 g pad of silica gel washing with dichloromethane (˜1 L) and the filtrate was concentrated to give the desired benzofuran (64 g, 56%) as an orange solid, mp 107–111° C. 1H NMR δ (CDCl3) 7.50 (s, 1H), 7.23 (d, 1H), 7.03 (d, 1H), 3.98 (s, 3H), 3.82 (s, 3H).

후처리

  1. temperatureThe reaction was heated
  2. temperatureat reflux under a Dean-Stark trap for 48 h
  3. concentrationThe reaction was concentrated
  4. dissolutionthe residue dissolved with dichloromethane (−0.5 L)
  5. filtrationfiltered through Celite
  6. washwashing with dichloromethane (˜0.5 L)
  7. washThe filtrate was washed with 1 L of 1M sodium hydroxide and water (2×1 L)
  8. concentrationthe filtrate was concentrated

출처 및 근거

ORD 기록
ord-4168c7d6c6a6492c9e5012519517523b
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07094798B1

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