Sodium Iodide → [2-(4-Ethoxyphenyl)-2-trifluoromethylpropyl](4-fluoro-3-phenoxybenzyl)ether

HRID 414278Notes

Reaction equation

HRID 414278 reaction equation
[H-].[Na+].[CH2:3]([O:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]([C:16]([F:19])([F:18])[F:17])([CH3:15])[CH2:13][OH:14])=[CH:8][CH:7]=1)[CH3:4].[I-].[Na+].[F:22][C:23]1[CH:30]=[CH:29][C:26]([CH2:27]Br)=[CH:25][C:24]=1[O:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1>C(COC)OC>[CH2:3]([O:5][C:6]1[CH:7]=[CH:8][C:9]([C:12]([C:16]([F:17])([F:18])[F:19])([CH3:15])[CH2:13][O:14][CH2:27][C:26]2[CH:29]=[CH:30][C:23]([F:22])=[C:24]([O:31][C:32]3[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=3)[CH:25]=2)=[CH:10][CH:11]=1)[CH3:4]

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 24758Sodium hydrideHCID 129227144-(Bromomethyl)-1-fluoro-2-phenoxybenzeneHCID 212521792-(4-Ethoxyphenyl)-2-trifluoromethyl-1-propanol

Product 1

HCID 13885605[2-(4-Ethoxyphenyl)-2-trifluoromethylpropyl](4-fluoro-3-phenoxybenzyl)etherYield 91.1%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

Sodium hydride (144 mg; 6 mmol) was suspended in dimethoxyethane (16 ml) and then in turn, with stirring, there was added 2-(4-ethoxyphenyl)-2-trifluoromethyl-1-propanol (1.25 g; 5.044 mmol), a spatula of sodium iodide and 4-fluoro-3-phenoxybenzyl bromide (1.4 g; 5.04 mmol). After stirring for 5 hours at room temperature, the mixture was added to ice-water, extracted 3 times with ether and the extracts washed with water dried over sodium sulphate and evaporated. After chromatography on silica gel using a mixture of ethyl acetate and hexane, there was obtained 2.06 g of product (=91.1% of theory).

Workup

  1. stirringAfter stirring for 5 hours at room temperature
  2. extractionextracted 3 times with ether
  3. washthe extracts washed with water
  4. dry with materialdried over sodium sulphate
  5. customevaporated
  6. additionAfter chromatography on silica gel using a mixture of ethyl acetate and hexane

Sources & evidence

ORD record
ord-c5458421beac43188a92b551ce80fcd3
Source dataset
uspto-grants-1988_12
Patent number
US04791123

Reaction notes

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