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

HRID 1896796Notes

Reaction equation

HRID 1896796 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-3954e09c79a14f3e808f585f4d59d02d
Source dataset
uspto-grants-2013_08
Patent number
US08518985B2

Reaction notes

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