Sodium Iodide → HCID 13885607, compound

HRID 414281Notes

Reaction equation

HRID 414281 reaction equation
[H-].[Na+].[C:3]1([CH:9]([C:12]([F:15])([F:14])[F:13])[CH2:10][OH:11])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[I-].[Na+].[O:18]([C:25]1[CH:26]=[C:27]([CH:30]=[CH:31][CH:32]=1)[CH2:28]Br)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>C(COC)OC>[C:3]1([CH:9]([C:12]([F:13])([F:14])[F:15])[CH2:10][O:11][CH2:28][C:27]2[CH:30]=[CH:31][CH:32]=[C:25]([O:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH:26]=2)[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 24758Sodium hydrideHCID 945441-(Bromomethyl)-3-phenoxybenzeneHCID 14205782113242-93-6

Product 1

HCID 13885607HCID 13885607, compoundYield 58.3%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

Sodium hydride (138 mg; 5.75 mmol) was suspended in dimethoxyethane (20 ml). There was then added in turn, with stirring, 2-phenyl-2-trifluoromethylethanol (1.0 g; 5.25 mmol), a spatula full of sodium iodide and 3-phenoxybenzyl bromide (1.39 g; 5.25 mmol). After stirring for 4 hours at room temperature, the mixture was added to ice-water, extracted with ether, the extract washed with water, dried over sodium sulphate and concentrated. After chromatogrpahy on silica gel using a mixture of hexane and toluene, there was obtained 1.14 g of product (=58.3% of theory).

Workup

  1. additionThere was then added in turn
  2. stirringAfter stirring for 4 hours at room temperature
  3. extractionextracted with ether
  4. washthe extract washed with water
  5. dry with materialdried over sodium sulphate
  6. concentrationconcentrated
  7. additionAfter chromatogrpahy on silica gel using a mixture of hexane and toluene

Sources & evidence

ORD record
ord-751bf79a966648d9adce1460750ec299
Source dataset
uspto-grants-1988_12
Patent number
US04791123

Reaction notes

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