Water → HCID 22731430, compound

HRID 1356726Notes

Reaction equation

HRID 1356726 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([CH:10]=[CH:11][C:12]=1[F:13])[CH2:8]Br)([CH3:4])([CH3:3])[CH3:2].[I-:14].[Na+].O>CC(C)=O>[C:1]([C:5]1[CH:6]=[C:7]([CH:10]=[CH:11][C:12]=1[F:13])[CH2:8][I:14])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 962WaterHCID 5238Sodium IodideHCID 22731428HCID 22731428, compound

Product 1

HCID 22731430HCID 22731430, compoundYield 66.4%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 3-tert-butyl-4-fluorobenzyl bromide (1.49 g, 6.08 mmol) in acetone (50 ml), sodium iodide (9.1 g, 60.8 mmol) was added, followed by stirring at room temperature overnight. The reaction mixture was mixed with water and extracted with n-hexane. The organic layer was washed with an aqueous sodium thiosulfate solution and saturated brine, dried over sodium sulfate and evaporated under reduced pressure to remove the solvent. The thus obtained residue was subjected to silica gel column chromatography (developing solvent: n-hexane) to give the titled compound (1.18 g, 66%).

Workup

  1. extractionextracted with n-hexane
  2. washThe organic layer was washed with an aqueous sodium thiosulfate solution and saturated brine
  3. dry with materialdried over sodium sulfate
  4. customevaporated under reduced pressure
  5. customto remove the solvent

Sources & evidence

ORD record
ord-dab61d045eb74b38859080a3803eb3b2
Source dataset
uspto-grants-2003_07
Patent number
US06586630B1

Reaction notes

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