Cesium carbonate → 3-(Difluoromethoxy)bromobenzene

HRID 404347노트

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HRID 404347 반응식
[Br:1][C:2]1[CH:3]=[C:4]([OH:8])[CH:5]=[CH:6][CH:7]=1.Cl[C:10]([F:15])([F:14])C([O-])=O.[Na+].C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C.CCOC(C)=O>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([O:8][CH:10]([F:15])[F:14])[CH:3]=1

참가 물질

6

반응물 3

HCID 10796Cesium carbonateHCID 115633-BromophenolHCID 2734985Sodium chlorodifluoroacetate

생성물 1

HCID 27370063-(Difluoromethoxy)bromobenzene수율 61%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

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온도
100 °C

실험 절차

To a solution of 3-bromophenol (commercially available from Sigma-Aldrich, St. Louis, Mo., USA) (1.28 g, 7.39 mmol) in DMF (12.0 mL) was added sodium 2-chloro-2,2-difluoroacetate (commercially available from Sigma-Aldrich, St. Louis, Mo., USA) (2.82 g, 18.49 mmol) and Cs2CO3 (4.82 g, 14.79 mmol). The reaction mixture was heated at 100° C. Gas was released from the reaction so care should be taken. After 2 hours, the reaction was cooled to room temperature then diluted with EtOAc, washed with water and then brine and re-extracted three times with EtOAc. The combined organic layers were dried over magnesium sulfate and then filtered, concentrated, and purified with silica gel chromatography (0-5% EtOAc in hexanes) to yield T18.1 as an oil that was used without further purification (yield 61%).

후처리

  1. customGas was released from the reaction so care
  2. temperaturethe reaction was cooled to room temperature
  3. washwashed with water
  4. extractionbrine and re-extracted three times with EtOAc
  5. dry with materialThe combined organic layers were dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. custompurified with silica gel chromatography (0-5% EtOAc in hexanes)
  9. customto yield T18.1 as an oil that
  10. customwas used without further purification (yield 61%)

출처 및 근거

ORD 기록
ord-a49ad95c5cf94cbcab67e7efa6b6d28c
출처 데이터셋
uspto-grants-2014_06
특허 번호
US08748462B2

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