2,2,2-Trifluoroethanol → 2,6-Dimethyl-4-trifluoroethoxyphenylacetic acid

HRID 2167124Notes

Reaction equation

HRID 2167124 reaction equation
[H-].[Na+].[CH2:3]([OH:8])[C:4]([F:7])([F:6])[F:5].[CH3:9][C:10]1[CH:15]=[C:14](Br)[CH:13]=[C:12]([CH3:17])[C:11]=1[CH2:18][C:19]([O:21]C)=[O:20]>CN(C=O)C.[Cu]I>[CH3:17][C:12]1[CH:13]=[C:14]([O:8][CH2:3][C:4]([F:7])([F:6])[F:5])[CH:15]=[C:10]([CH3:9])[C:11]=1[CH2:18][C:19]([OH:21])=[O:20]

Participants

6

Reactant 3

HCID 64092,2,2-TrifluoroethanolHCID 24758Sodium hydrideHCID 22889389Methyl 2-(4-bromo-2,6-dimethylphenyl)acetate

Product 1

HCID 596120672,6-Dimethyl-4-trifluoroethoxyphenylacetic acid

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 6228DimethylformamideSolvent2×

Procedure

18.05 g (451 mmol) of sodium hydride are initially charged in 500 ml of DMF, 41.05 g (410 mmol) of trifluoroethanol are added dropwise, after the evolution of gas has ended 15.63 g (82 mmol) of copper(I) iodide are added, a solution of 21.10 g (82 mmol) of methyl 2,6-dimethyl-4-bromophenylacetate in 100 ml of DMF is slowly added dropwise and the mixture is boiled at reflux for 2.5 h.

Workup

  1. additionare added
  2. temperatureat reflux for 2.5 h.

Sources & evidence

ORD record
ord-9c331abead024840a322156aeed1d8dd
Source dataset
uspto-grants-2015_06
Patent number
US09045390B2

Reaction notes

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