Chloride → 3,5-Bis(trifluoromethyl)styrene

HRID 2186442Notes

Reaction equation

HRID 2186442 reaction equation
[F:1][C:2]([F:15])([F:14])[C:3]1[CH:4]=[C:5](Br)[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.[Cl-].[CH2:17](N(CC)CC)[CH3:18].C=C>C(#N)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.CCCCC>[F:1][C:2]([F:15])([F:14])[C:3]1[CH:4]=[C:5]([CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1)[CH:17]=[CH2:18]

Participants

8

Reactant 4

HCID 312ChlorideHCID 6325EthyleneHCID 8471TriethylamineHCID 676021-Bromo-3,5-bis(trifluoromethyl)benzene

Product 1

HCID 27732423,5-Bis(trifluoromethyl)styreneYield 95%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 6342AcetonitrileSolventHCID 8003PentaneSolvent

Conditions

Temperature
80 °C

Procedure

A solution of 3,5-bis(trifluoromethyl)-1-bromobenzene (75 g, 0.256 mol), tetiabutylammonium chloride (71.4 g, 0.256 mol), triethylamine (71.3 mL, 0.97 mol) and palladium(II) acetate (113 mg) in acetonitrile (360 mL) was deoxygenated with a vigorous flow of nitrogen. The reaction was pressurized with ethylene (950 psi) and heated to 80° C. for 36 hours. Pentane (400 mL) was added and after 3 water washes (200 mL) the organic layer was dried over Na2SO4 and the solvent was removed in vacuo to afford 3,5-bis(trifluoromethyl)styrene as a pale yellow oil (58.2 g, 0.242 mol, 95% yield).

Workup

  1. dry with materialafter 3 water washes (200 mL) the organic layer was dried over Na2SO4
  2. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-476ed8c96a304c0c82c4087d5bbe89b7
Source dataset
uspto-grants-2002_06
Patent number
US06403793B2

Reaction notes

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