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

HRID 535265

Reaction equation

HRID 535265 reaction equation
[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

Participants

7

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
110 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-ee84e78adf8f46ed9d0860a704466fc9
Source dataset
uspto-grants-2014_10
Patent number
US08859494B2

Linked notes

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