p-Fluorotoluene → HCID 22731437, compound

HRID 1356724Notes

Reaction equation

HRID 1356724 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[F:5][C:6]1[CH:11]=[CH:10][C:9]([CH3:12])=[CH:8][CH:7]=1.[C:13](Cl)([CH3:16])([CH3:15])[CH3:14]>C(=S)=S>[C:13]([C:7]1[CH:8]=[C:9]([CH3:12])[CH:10]=[CH:11][C:6]=1[F:5])([CH3:16])([CH3:15])[CH3:14]

Participants

5

Reactant 3

HCID 9603p-FluorotolueneHCID 10486tert-BUTYL CHLORIDEHCID 6451240Aluminum(III) Chloride

Product 1

HCID 22731437HCID 22731437, compoundYield 65.3%

Reagents, catalysts & solvents 1

HCID 6348Carbon DisulfideSolvent

Procedure

To a solution of aluminum chloride (8.1 g, 60.7 mmol) in carbon disulfide (60 ml), 4-fluorotoluene (6.0 g, 54.5 mmol) was added and then under cooling with ice, tert-butyl chloride (6.0 ml, 54.5 mmol) was added, followed by stirring for 10 min. The reaction mixture was poured into ice water and extracted with methylene chloride. The organic layer was washed with 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 (5.92 g, 63%).

Workup

  1. additionwas added
  2. extractionextracted with methylene chloride
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over sodium sulfate
  5. customevaporated under reduced pressure
  6. customto remove the solvent

Sources & evidence

ORD record
ord-660ca243c92b42c99675777d275b3cdb
Source dataset
uspto-grants-2003_07
Patent number
US06586630B1

Reaction notes

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