Monobenzone → 1-(Benzyloxy)-4-(2,2,2-trifluoroethoxy)benzene

HRID 51077노트

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HRID 51077 반응식
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[Cs+].[Cs+].FC(F)(F)S(O[CH2:28][C:29]([F:32])([F:31])[F:30])(=O)=O>CN(C=O)C>[F:30][C:29]([F:32])([F:31])[CH2:28][O:15][C:12]1[CH:11]=[CH:10][C:9]([O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[CH:14][CH:13]=1

참가 물질

5

반응물 3

HCID 7638MonobenzoneHCID 10796Cesium carbonateHCID 803662,2,2-Trifluoroethyl trifluoromethanesulfonate

생성물 1

HCID 227373741-(Benzyloxy)-4-(2,2,2-trifluoroethoxy)benzene수율 106.1%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
50 °C

실험 절차

To a 20 ml DMF solution of 4-benzyloxyphenol (3.35 g, 16.7 mmol) and cesium carbonate (6.02 g, 18.5 mmol) was added 2,2,2-trifluoroethyl trifluoromethanesulfonate (4.29 g, 18.4 mmol) upon cooling in an ice-water bath. The cooling bath was removed and the reaction mixture was heated to 50° C. for 1 hr. The reaction mixture was diluted with AcOEt and water. The organic layer was separated, washed with 1N hydrochloric acid, dried over anhydrous Na2SO4, filtered, and concentrated to give benzyl 4-(2,2,2-trifluoroethoxy)phenyl ether 5.0 g (quant.). This material was dissolved in 200 ml of ethanol and was hydrogenated in a Parr shaker with 10% Pd/C 222 mg under hydrogen atmosphere (50 psi) overnight. The catalyst was removed by suction filtration through a pad of celite. The filtrate was concentrated to give the title compound 2.6 g (87%).

후처리

  1. temperatureupon cooling in an ice-water bath
  2. customThe cooling bath was removed
  3. additionThe reaction mixture was diluted with AcOEt and water
  4. customThe organic layer was separated
  5. washwashed with 1N hydrochloric acid
  6. dry with materialdried over anhydrous Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated

출처 및 근거

ORD 기록
ord-deffc2e1647747308a86e634947a8d29
출처 데이터셋
uspto-grants-2004_03
특허 번호
US06713508B2

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