Ethynylcyclohexane → 1-Cyclohexylethynyl-3-trifluoromethyl-benzene

HRID 451263Notes

Reaction equation

HRID 451263 reaction equation
[F:1][C:2]([F:21])([F:20])[C:3]1[CH:4]=[C:5](OS(C2C=CC(C)=CC=2)(=O)=O)[CH:6]=[CH:7][CH:8]=1.[C:22]([CH:24]1[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]1)#[CH:23]>CCCCCCC>[CH:24]1([C:22]#[C:23][C:5]2[CH:6]=[CH:7][CH:8]=[C:3]([C:2]([F:1])([F:20])[F:21])[CH:4]=2)[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]1

Participants

4

Reactant 2

HCID 70263EthynylcyclohexaneHCID 112439861-(Tosyloxy)-3-(trifluoromethyl)benzene

Product 1

HCID 252216101-Cyclohexylethynyl-3-trifluoromethyl-benzene

Reagents, catalysts & solvents 1

HCID 8900HeptaneSolvent

Procedure

This product was prepared from toluene-4-sulfonic acid 3-trifluoromethyl-phenyl ester and ethynyl-cyclohexane following the general procedure for the Sonogashira cross-coupling process described above. Chromatography eluent: heptane; yield (82 mg, 65%); δH (CDCl3): 7.67 (s, 1H), 7.61-7.7.49 (m, 2H), 7.46-7.37 (m, 1H), 2.70-2.52 (m, 1H), 2.04-1.30 (m, 10H); LCMS m/z: 252.

Workup

  1. customyield (82 mg, 65%)

Sources & evidence

ORD record
ord-81cf106f1bf84d18bd54591aa1a577e9
Source dataset
uspto-grants-2013_07
Patent number
US08487109B2

Reaction notes

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