Potassium Carbonate → 6-Bromo-4-(4-hydroxy-benzyl)-7-methoxy-3-(4-trifluoromethyl-phenyl)-chromen-2-one

HRID 1296696노트

반응식

HRID 1296696 반응식
[Br:1][C:2]1[C:3]([O:19][CH3:20])=[CH:4][C:5]([OH:18])=[C:6]([C:8](=O)[CH2:9][C:10]2[CH:15]=[CH:14][C:13]([OH:16])=[CH:12][CH:11]=2)[CH:7]=1.[F:21][C:22]([F:34])([F:33])[C:23]1[CH:28]=[CH:27][C:26]([CH2:29][C:30](O)=[O:31])=[CH:25][CH:24]=1.C(C1NC=CN=1)(C1NC=CN=1)=O.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.O>[Br:1][C:2]1[CH:7]=[C:6]2[C:5](=[CH:4][C:3]=1[O:19][CH3:20])[O:18][C:30](=[O:31])[C:29]([C:26]1[CH:25]=[CH:24][C:23]([C:22]([F:21])([F:33])[F:34])=[CH:28][CH:27]=1)=[C:8]2[CH2:9][C:10]1[CH:15]=[CH:14][C:13]([OH:16])=[CH:12][CH:11]=1

참가 물질

7

반응물 4

HCID 11430Potassium CarbonateHCID 118342(alpha,alpha,alpha-Trifluoro-4-tolyl)acetic acidHCID 5250894Bis-(1H-imidazol-2-YL)-methanoneHCID 589131241-(5-Bromo-2-hydroxy-4-methoxy-phenyl)-2-(4-hydroxy-phenyl)-ethanone

생성물 1

HCID 589131126-Bromo-4-(4-hydroxy-benzyl)-7-methoxy-3-(4-trifluoromethyl-phenyl)-chromen-2-one수율 85.4%

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

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온도
80 °C

실험 절차

A mixture of 1-(5-bromo-2-hydroxy-4-methoxy-phenyl)-2-(4-hydroxy-phenyl)-ethanone (0.64 g, 1.9 mmol), 4-trifluoromethylphenylacetic acid (0.78 g, 3.8 mmol), carbonyl diimidazole (0.62 g, 3.8 mmol), N,N-dimethylaminopyridine (0.12 g, 1.0 mmol), and potassium carbonate (0.52 g, 3.8 mmol) in DMF (15 mL) was heated within an 80° C. oil bath overnight. The cooled reaction mixture was poured into water and extracted with EtOAc. Organic extracts were combined and washed with water and saturated sodium chloride in succession, dried over magnesium sulfate, filtered and concentrated under reduced pressure. The resulting material purified using silica gel flash column chromatography (1:2 EtOAc:hexanes) to provide the title compound (0.82 g, 85%). MS (ESI) m/z 505.0 (M+1)+, 507.0 (M+1+2)+.

후처리

  1. customThe cooled reaction mixture
  2. extractionextracted with EtOAc
  3. washwashed with water and saturated sodium chloride in succession
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe resulting material purified

출처 및 근거

ORD 기록
ord-f74eb17b4620424ab11034f3612f1096
출처 데이터셋
uspto-grants-2007_07
특허 번호
US07247646B2

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