3-(Trifluoromethyl)phenol → HCID 19044668, compound

HRID 1682530Notes

Reaction equation

HRID 1682530 reaction equation
[CH3:1][C:2]1[N:7]=[C:6](Cl)[C:5]([CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:4][N:3]=1.[F:15][C:16]([F:25])([F:24])[C:17]1[CH:18]=[C:19]([OH:23])[CH:20]=[CH:21][CH:22]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.CCOCC>[CH3:1][C:2]1[N:7]=[C:6]([O:23][C:19]2[CH:20]=[CH:21][CH:22]=[C:17]([C:16]([F:15])([F:24])[F:25])[CH:18]=2)[C:5]([CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:4][N:3]=1

Participants

6

Reactant 3

HCID 73763-(Trifluoromethyl)phenolHCID 11430Potassium CarbonateHCID 26604(6-Chloro-2-methyl-5-pyrimidyl)acetic acid, ethyl ester

Product 1

HCID 19044668HCID 19044668, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

Ethyl α-(2-methyl-4-chloro-5-pyrimidinyl)-acetate (3 g, 14 mmol), 3-trifluoromethyl phenol (3 g, 14 mmol) and potassium carbonate (11 g, 80 mmol) in dimethylformamide (50 ml) are stirred at +80° C. for 3 hours. The mixture is diluted with ether and washed with brine. Drying over MgSO4 and evaporation of the solvent gives pure ethyl α-[2-methyl-4-(3-trifluoromethylphenoxy)-5-pyrimidinyl]-acetate as an oil. 1H(CDCl3); 8.36 (s, 1H); 7.50-7.25 (m, 4H); 3.90 (s, 2H); 3.85 (s, 3H); 2.5 (s, 3H).

Workup

  1. washwashed with brine
  2. dry with materialDrying over MgSO4 and evaporation of the solvent

Sources & evidence

ORD record
ord-28c4ff9c7b1647669fbaa6a62cab97aa
Source dataset
uspto-grants-1997_06
Patent number
US05635508

Reaction notes

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