p-Fluoronitrobenzene → 1-Fluoro-4-(4-nitrophenoxy)-2-(trifluoromethyl)benzene

HRID 2237007

반응식

HRID 2237007 반응식
F[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][CH:3]=1.[F:11][C:12]1[CH:18]=[CH:17][C:15]([O-:16])=[CH:14][C:13]=1[C:19]([F:22])([F:21])[F:20].[K+].CC(C)([O-])C.[K+]>C1COCC1>[F:11][C:12]1[CH:18]=[CH:17][C:15]([O:16][C:2]2[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][CH:3]=2)=[CH:14][C:13]=1[C:19]([F:20])([F:21])[F:22]

참가 물질

5

반응물 3

HCID 9590p-FluoronitrobenzeneHCID 23665647Potassium tert-butoxideHCID 23697190Potassium 4-fluoro-3-trifluoromethyl-phenoxide

생성물 1

HCID 669776401-Fluoro-4-(4-nitrophenoxy)-2-(trifluoromethyl)benzene

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매3회

반응 조건

온도
0 °C

실험 절차

To a stirred solution of 4-fluoronitrobenzene (2.0 mmol) in anhydrous THF (5 mL) at 0° C., a 1M solution of a potassium 4-fluoro-3-trifluoromethyl-phenoxide (2.2 mmol) in THF (may be generated by adding the corresponding alcohol to a 1M solution of potassium t-butoxide in THF) was added dropwise and under a nitrogen stream, according to General Procedure L1. The reaction mixture was stirred at 0° C. until completion, as indicated by TLC or HPLC. The solvent was then removed in vacuuo and the reaction mixture was treated with cold H2O (15 mL), and extracted with EtOAc (2×15 mL). The combined organic layers were washed with brine and dried over sodium sulfate. Evaporation of the solvent in vacuuo afforded the desired 1-fluoro-4-(4-nitrophenoxy)-2-(trifluoromethyl)benzene. The crude product could be used directly for further transformation .

후처리

  1. customat 0° C.
  2. additionwas added dropwise and under a nitrogen stream
  3. customThe solvent was then removed in vacuuo
  4. additionthe reaction mixture was treated with cold H2O (15 mL)
  5. extractionextracted with EtOAc (2×15 mL)
  6. washThe combined organic layers were washed with brine
  7. dry with materialdried over sodium sulfate
  8. customEvaporation of the solvent in vacuuo

출처 및 근거

ORD 기록
ord-3f48445bfa164cf2bc63883e2c481c15
출처 데이터셋
uspto-grants-2010_05
특허 번호
US07714013B2

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