Potassium Carbonate → 4-Fluoro-3-phenoxybenzyl 3-(2,2,2-trifluoroethoxy)-2,2-dimethylcyclopropanecarboxylate

HRID 28097Notes

Reaction equation

HRID 28097 reaction equation
[F:1][C:2]([F:14])([F:13])[CH2:3][O:4][CH:5]1[CH:7]([C:8]([OH:10])=[O:9])[C:6]1([CH3:12])[CH3:11].C(=O)([O-])[O-].[K+].[K+].[F:21][C:22]1[CH:29]=[CH:28][C:25]([CH2:26]Br)=[CH:24][C:23]=1[O:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1>CN(C=O)C>[F:1][C:2]([F:13])([F:14])[CH2:3][O:4][CH:5]1[CH:7]([C:8]([O:10][CH2:26][C:25]2[CH:28]=[CH:29][C:22]([F:21])=[C:23]([O:30][C:31]3[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=3)[CH:24]=2)=[O:9])[C:6]1([CH3:11])[CH3:12]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 129227144-(Bromomethyl)-1-fluoro-2-phenoxybenzeneHCID 203049423-(2,2,2-Trifluoroethoxy)-2,2-dimethylcyclopropanecarboxylic acid

Product 1

HCID 233388534-Fluoro-3-phenoxybenzyl 3-(2,2,2-trifluoroethoxy)-2,2-dimethylcyclopropanecarboxylate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To 10 ml DMF is added 0.88 g 3-(2,2,2-trifluoroethoxy)-2,2-dimethylcyclopropanecarboxylic acid (4.14 mmol) and 1.146 g potassium carbonate (8.29 mmol), after which is added 1.2 g 4-fluoro-3-phenoxybenzyl bromide. This mixture is stirred under nitrogen for 15 hours. The reaction mixture is extracted with ether and the ether phase is washed with water (3×) and brine, and dried over sodium sulfate. The solvent is then removed to yield 4-fluoro-3-phenoxybenzyl 3-(2,2,2-trifluoroethoxy)-2,2-dimethylcyclopropanecarboxylate.

Workup

  1. extractionThe reaction mixture is extracted with ether
  2. washthe ether phase is washed with water (3×) and brine
  3. dry with materialdried over sodium sulfate
  4. customThe solvent is then removed

Sources & evidence

ORD record
ord-dfc4b1cbe6db4f458c523cef4111373f
Source dataset
uspto-grants-1980_09
Patent number
US04225533

Reaction notes

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