Potassium Carbonate → [4-Chloro-3-(2,2,2-trifluoroethoxy)phenyl]methanol

HRID 514531Notes

Reaction equation

HRID 514531 reaction equation
CC1C=CC(S(O[CH2:12][C:13]([F:16])([F:15])[F:14])(=O)=O)=CC=1.[Cl:17][C:18]1[CH:23]=[CH:22][C:21]([CH2:24][OH:25])=[CH:20][C:19]=1[OH:26].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[Cl:17][C:18]1[CH:23]=[CH:22][C:21]([CH2:24][OH:25])=[CH:20][C:19]=1[O:26][CH2:12][C:13]([F:16])([F:15])[F:14]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 67942Ethanol, 2,2,2-trifluoro-, 1-(4-methylbenzenesulfonate)HCID 684658332-Chloro-5-(hydroxymethyl)phenol

Product 1

HCID 86725642[4-Chloro-3-(2,2,2-trifluoroethoxy)phenyl]methanolYield 75%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 2,2,2-trifluoroethyl 4-methylbenzenesulfonate (1.34 g, 5.28 mmol), 2-chloro-5-(hydroxymethyl)phenol (837 mg, 5.28 mmol), K2CO3 (1.46 g, 10.56 mmol) and DMF (9 mL) was heated to 100° C. overnight. It was then poured into ice-water and extracted with ethyl acetate twice. Organic phase washed with water twice, brine and dried with Na2SO4, concentrated to a residue which was purified by flash column chromatograph to give the title compound (903 mg, 75%). 1H NMR (400 MHz, CDCl3): δ 1.77 (1H, t, J=5.6 Hz), 4.42 (2H, q, J=8.0 Hz), 4.68 (2H, d, J=5.2 Hz), 6.99 (1H, dd, J=1.6 Hz, 8.0 Hz), 7.02 (1H, s), 7.37 (1H, d, J=8.0 Hz).

Workup

  1. extractionextracted with ethyl acetate twice
  2. washOrganic phase washed with water twice
  3. dry with materialbrine and dried with Na2SO4
  4. concentrationconcentrated to a residue which
  5. customwas purified by flash column chromatograph

Sources & evidence

ORD record
ord-5b786890e6d54746ab5a8729bcef50cc
Source dataset
uspto-grants-2015_08
Patent number
US09107916B2

Reaction notes

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