1-Chloro-4-(trifluoromethyl)benzene → 4-trifluoromethyl-cinnamic Acid Butyl Ester

HRID 1837803Notes

Reaction equation

Cl[C:2]1[CH:7]=[CH:6][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:4][CH:3]=1.[CH2:12]([O:16][C:17](=[O:20])[CH:18]=[CH2:19])[CH2:13][CH2:14][CH3:15].C(=O)([O-])[O-].[Na+].[Na+].C12(PC34CC(CC3)CC4)CC(CC1)CC2>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.CC(N(C)C)=O.Cl[Pd]Cl>[CH2:12]([O:16][C:17](=[O:20])[CH:18]=[CH:19][C:2]1[CH:7]=[CH:6][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:4][CH:3]=1)[CH2:13][CH2:14][CH3:15]

Participants

Conditions

Temperature: 130 °C

Procedure

4-chlorobenzotrifluoride (0.71 g, 5 mmols), acrylic acid butyl ester (0.97 g, 7.6 mmols), sodium carbonate (0.81 g, 7.6 mmols), tetrabutylammonium bromide (161 mg, 0.5 mmol) and 4 ml DMA are placed under argon in a reaction flask and heated to 130° C. Afterwards, 22 mg of dinorbornyl phosphine in 1 ml of DMA and 0.2 ml of a 0.25 M PdCl2 solution in DMA are dispensed in after one another. The reaction mixture is stirred for 10 hours at 130° C. and then cooled. The yield determined in the reaction mixture by gas chromatography is 95% (GC).

Workup

temperaturecooled

Sources & evidence

ORD record: ord-2f5ad00b1475446da6a4f6fd73c18da0
Source dataset: uspto-grants-2004_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06784295B2

Reaction notes

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