Water → [3-(2-Chloro-4-trifluoromethylphenoxymethyl)oxetan-3-yl]-methanol

HRID 535265

반응식

HRID 535265 반응식
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]([F:12])([F:11])[F:10])[CH:5]=[CH:6][C:7]=1[OH:8].Br[CH2:14][C:15]1([CH2:19][OH:20])[CH2:18][O:17][CH2:16]1.C(=O)([O-])[O-].[Cs+].[Cs+].O>C(#N)C.C(OCC)(=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([C:9]([F:10])([F:11])[F:12])[CH:5]=[CH:6][C:7]=1[O:8][CH2:14][C:15]1([CH2:19][OH:20])[CH2:18][O:17][CH2:16]1

참가 물질

7

반응물 4

HCID 962WaterHCID 10796Cesium carbonateHCID 529264[3-(Bromomethyl)oxetan-3-yl]methanolHCID 27366032-Chloro-4-(trifluoromethyl)phenol

생성물 1

HCID 58031838[3-(2-Chloro-4-trifluoromethylphenoxymethyl)oxetan-3-yl]-methanol

시약·촉매·용매 2

HCID 6342Acetonitrile용매HCID 8857Ethyl Acetate용매

반응 조건

온도
110 °C

실험 절차

600 mg of 3-chloro-4-hydroxybenzotrifluoride and 829 mg of 3-bromomethyl-3-oxetanemethanol were dissolved in 20 ml of acetonitrile, and 1.49 g of cesium carbonate were added. The reaction mixture was heated to 110° C. and stirred at this temperature for three hours. 50 ml of water and 50 ml of ethyl acetate were added to the cooled reaction mixture. The organic phase was removed, dried over MgSO4 and then concentrated under reduced pressure. The residue was purified on silica gel with the n-heptane/ethyl acetate solvent mixture as a linear gradient of 100% n-heptane=>100% ethyl acetate. This gave 990 mg of [3-(2-chloro-4-trifluoromethylphenoxymethyl)oxetan-3-yl]methanol.

후처리

  1. customThe organic phase was removed
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified on silica gel with the n-heptane/ethyl acetate solvent mixture as a linear gradient of 100% n-heptane=>100% ethyl acetate

출처 및 근거

ORD 기록
ord-ee84e78adf8f46ed9d0860a704466fc9
출처 데이터셋
uspto-grants-2014_10
특허 번호
US08859494B2

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