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

HRID 1420819ノート

反応式

HRID 1420819 の反応式
[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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
50 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-7ad5ab7cb5ca4ad9a0fe1c0bd42303ce
出典データセット
uspto-grants-2000_06
特許番号
US06071927

反応ノート

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