Dichloromethane → 1-Isopropenyl-4-(2,2,2-trifluoro-1,1-dimethylethyl)benzene

HRID 1438382Notes

Reaction equation

HRID 1438382 reaction equation
FC(F)(F)S(O[C:7]1[CH:12]=[CH:11][C:10]([C:13]([CH3:19])([CH3:18])[C:14]([F:17])([F:16])[F:15])=[CH:9][CH:8]=1)(=O)=O.[C:22]([B-](F)(F)F)([CH3:24])=[CH2:23].[K+].C(Cl)Cl.C(N(CC)CC)C>C(O)CC.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[C:22]([C:7]1[CH:12]=[CH:11][C:10]([C:13]([CH3:19])([CH3:18])[C:14]([F:17])([F:16])[F:15])=[CH:9][CH:8]=1)([CH3:24])=[CH2:23]

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 8471TriethylamineHCID 23670158Potassium (prop-1-en-2-yl)trifluoroborateHCID 866390464-(2,2,2-Trifluoro-1,1-dimethylethyl)Phenyl trifluoromethanesulfonate

Product 1

HCID 670474241-Isopropenyl-4-(2,2,2-trifluoro-1,1-dimethylethyl)benzeneYield 70%

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 10311-PropanolSolvent

Procedure

The procedure described in Example 10B was followed using a mixture of 4-(2,2,2-trifluoro-1,1-dimethylethyl)phenyl trifluoromethanesulfonate (13.3 g, 40 mmol), potassium isopropenyltrifluoroborate (7.0 g, 47.6 mmol), PdCl2(dppf).CH2Cl2 (1.6 g, 1.98 mmol) and triethylamine (5.5 ml, 40 mmol) in n-propanol (400 ml). The crude residue was applied to a silica gel chromatography column and eluted with a volume mixture of hexane and EtOAc (100/1) to afford 6.32 g (70% yield) of the title compound as a colorless oil.

Workup

  1. washeluted with a volume mixture of hexane and EtOAc (100/1)

Sources & evidence

ORD record
ord-8564246158a94c56b183f4d26c8a679d
Source dataset
uspto-grants-2009_11
Patent number
US07622589B2

Reaction notes

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