Water → 2-[4-(4-Trifluoromethylpyridin-2-yloxy)-phenyl]-ethanol

HRID 339813Notes

Reaction equation

HRID 339813 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][OH:10])=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].F[C:18]1[CH:23]=[C:22]([C:24]([F:27])([F:26])[F:25])[CH:21]=[CH:20][N:19]=1.O>CS(C)=O>[F:25][C:24]([F:27])([F:26])[C:22]1[CH:21]=[CH:20][N:19]=[C:18]([O:1][C:2]2[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][OH:10])=[CH:4][CH:3]=2)[CH:23]=1

Participants

6

Reactant 4

HCID 962WaterHCID 10393TyrosolHCID 11430Potassium CarbonateHCID 111595142-Fluoro-4-(trifluoromethyl)pyridine

Product 1

HCID 581742462-[4-(4-Trifluoromethylpyridin-2-yloxy)-phenyl]-ethanolYield 75.4%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
25 °C

Procedure

2-(4-Hydroxyphenyl)ethanol (4.0 g, 29 mmol), K2CO3 (8.0 g, 58 mmol) and 2-fluoro-4-trifluoromethylpyridine (3.6 g, 22 mmol) were combined in DMSO (30 mL) and stirred at 25° C. for 20 h. The mixture was poured into H2O and extracted twice with Et2O. The combined Et2O extracts were washed with 1M NaOH, H2O, brine, and concentrated in vacuo to give 2-[4-(4-trifluoromethylpyridin-2-yloxy)-phenyl]-ethanol (4.7 g; 57%), mp 78-79° C.; EIMS m/z 283; 1H NMR (300 MHz, DMSO-d6) δ 8.38 (d, J=5.3 Hz, 1H), 7.0-7.5 (m, 8H), 4.67 (t, J=5.0 Hz, 2H), 2.74 (t, J=5.2 Hz, 2H).

Workup

  1. extractionextracted twice with Et2O
  2. washThe combined Et2O extracts were washed with 1M NaOH, H2O, brine
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-657573fce8ea451f8a3083ec107e46d2
Source dataset
uspto-grants-2014_11
Patent number
US08895568B2

Reaction notes

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