Water → 4-(2,6-Dichloro-4-trifluoromethylphenyl)toluene

HRID 498962Notes

Reaction equation

HRID 498962 reaction equation
I[C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][CH:3]=1.[Cl:9][C:10]1[CH:11]=[C:12]([C:18]([F:21])([F:20])[F:19])[CH:13]=[C:14]([Cl:17])[C:15]=1F.O>C1C=CC=CC=1.C([Li])CCC.CCCCCC.C(OCC)C>[Cl:9][C:10]1[CH:11]=[C:12]([C:18]([F:21])([F:20])[F:19])[CH:13]=[C:14]([Cl:17])[C:15]=1[C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][CH:3]=1

Participants

8

Reactant 3

HCID 962WaterHCID 122074-IodotolueneHCID 157026Benzene, 1,3-dichloro-2-fluoro-5-(trifluoromethyl)-

Product 1

HCID 221709614-(2,6-Dichloro-4-trifluoromethylphenyl)tolueneYield 85.1%

Reagents, catalysts & solvents 4

HCID 241BenzeneSolventHCID 3283Diethyl EtherSolventHCID 8058HexaneSolventHCID 178418339ButyllithiumSolvent

Procedure

To 5.7 g (26.1 mmol) of 4-iodotoluene in 30 ml of dry benzene, 17.0 ml of a n-butyllithium solution in hexane (1.60 mol/l) was added dropwise in a nitrogen stream at room temperature with stirring. After 2 hours of stirring at room temperature, 10 ml of 6.0 g (25.8 mmol) of 3,5-dichloro-4-fluorobenzotrifluoride in 10 ml of diethyl ether was added dropwise at 10° C. After another 12 hours of stirring at room temperature, the reaction mixture was poured into 100 ml of water for separation. The organic layer was washed with 50 ml of water twice and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure to obtain 6.7 g of 4-(2,6-dichloro-4-trifluoromethylphenyl)toluene (yield 85.0%) as a colorless liquid.

Workup

  1. stirringAfter 2 hours of stirring at room temperature
  2. stirringAfter another 12 hours of stirring at room temperature
  3. washThe organic layer was washed with 50 ml of water twice
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-f8616b7805cc4608b89eca5c0f3c0a1d
Source dataset
uspto-grants-2010_08
Patent number
US07767626B2

Reaction notes

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