Citric Acid → 2-Bromo-1-(cyclobutyloxy)-4-(trifluoromethoxy)benzene

HRID 1420819노트

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HRID 1420819 반응식
[Br:1][C:2]1[CH:7]=[C:6]([O:8][C:9]([F:12])([F:11])[F:10])[CH:5]=[CH:4][C:3]=1[OH:13].[CH:14]1(Br)[CH2:17][CH2:16][CH2:15]1.C(=O)([O-])[O-].[K+].[K+].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>CN(C)C=O>[Br:1][C:2]1[CH:7]=[C:6]([O:8][C:9]([F:11])([F:12])[F:10])[CH:5]=[CH:4][C:3]=1[O:13][CH:14]1[CH2:17][CH2:16][CH2:15]1

참가 물질

6

반응물 4

HCID 311Citric AcidHCID 11430Potassium CarbonateHCID 78110BromocyclobutaneHCID 215840902-Bromo-4-(trifluoromethoxy)phenol

생성물 1

HCID 538607702-Bromo-1-(cyclobutyloxy)-4-(trifluoromethoxy)benzene수율 91%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
50 °C

실험 절차

2-Bromo-4-(trifluoromethoxy)phenol (Description 11; 1.5 g, 5.83 mmol) and cyclobutyl bromide (3.0 g, 17.5 mmol) were dissolved in dimethylformamide (10 ml). Potassium carbonate (4.85 g, 35 mmol) was added and the solution was stirred at 50° C. for 16 h. The solution was allowed to cool to ambient temperature, poured into a 10% citric acid solution (50 ml) and extracted with ethyl acetate (2×100 ml). The combined organic layers were washed with water and dried over sodium sulphate. Removal of the solvent in vacuo gave an oil which was chromatographed on silica in 10% ethyl acetate/hexane to give the title compound as an oil (1.65 g, 91%). 1H NMR (250 MHz, CDCl3) δ7.44-7.42 (1H, m), 7.12-7.07 (1H, m), 6.73-6.70 (1H, d, J 9.0 Hz), 4.71-4.60 (1H, m), 2.52-2.41 (2H, m), 2.30-2.18 (2H, m), and 1.92-1.55 (2H, m).

후처리

  1. temperatureto cool to ambient temperature
  2. extractionextracted with ethyl acetate (2×100 ml)
  3. washThe combined organic layers were washed with water
  4. dry with materialdried over sodium sulphate
  5. customRemoval of the solvent in vacuo
  6. customgave an oil which
  7. customwas chromatographed on silica in 10% ethyl acetate/hexane

출처 및 근거

ORD 기록
ord-7ad5ab7cb5ca4ad9a0fe1c0bd42303ce
출처 데이터셋
uspto-grants-2000_06
특허 번호
US06071927

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