Potassium Carbonate → 3-(2-Chloro-4-fluorophenoxy)-1-(diphenylmethyl)azetidine

HRID 1053874

반응식

HRID 1053874 반응식
CS([O:5][CH:6]1[CH2:9][N:8]([CH:10]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH2:7]1)(=O)=O.C(=O)([O-])[O-].[K+].[K+].[Cl:29][C:30]1[CH:35]=[C:34]([F:36])[CH:33]=[CH:32][C:31]=1O>C(#N)C>[Cl:29][C:30]1[CH:35]=[C:34]([F:36])[CH:33]=[CH:32][C:31]=1[O:5][CH:6]1[CH2:9][N:8]([CH:10]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH2:7]1

참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 748142-Chloro-4-fluorophenolHCID 27587161-(Diphenylmethyl)azetidin-3-yl methanesulfonate

생성물 1

HCID 150422263-(2-Chloro-4-fluorophenoxy)-1-(diphenylmethyl)azetidine

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

A mixture of 1-(diphenylmethyl)-3-azetidinyl methanesulfonate (363.8 g, 1.15 mol), potassium carbonate (330 g, 2.38 mol) and 2-chloro-4-fluorophenol (140 g, 0.96 mol) in acetonitrile (2.5 L) was heated under reflux for 4.5 hours. The cooled reaction mixture was then concentrated in vacuo and the residue was partitioned between ethyl acetate (1 L) and water (500 mL). The organic layer was separated, dried over sodium sulfate concentrated in vacuo and the residue was triturated with ethyl acetate/pentane/dichloromethane, 90:10:1, to afford the title compound as a white solid in quantitative yield, 350 g. 1H NMR (400 MHz, CDCl3) δ: 3.19 (m, 2H), 3.75 (m, 2H), 4.45 (m, 1H), 4.78 (m, 1H), 6.60 (m, 1H), 6.83 (m, 1H), 7.14 (m, 1H), 7.18-7.50 (m, 10H)

후처리

  1. temperaturewas heated
  2. temperatureunder reflux for 4.5 hours
  3. customThe cooled reaction mixture
  4. concentrationwas then concentrated in vacuo
  5. customthe residue was partitioned between ethyl acetate (1 L) and water (500 mL)
  6. customThe organic layer was separated
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated in vacuo
  9. customthe residue was triturated with ethyl acetate/pentane/dichloromethane, 90:10:1

출처 및 근거

ORD 기록
ord-23b5ba0c61584af4965ac656c04f8753
출처 데이터셋
uspto-grants-2016_07
특허 번호
US09394278B2

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