5-Phenyl-1-pentyne → 1-(5-Phenyl-pent-1-ynyl)-3-trifluoromethyl-benzene

HRID 451262

Reaction equation

HRID 451262 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.[CH2:22]([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[CH2:23][CH2:24][C:25]#[CH:26]>CCCCCCC>[C:27]1([CH2:22][CH2:23][CH2:24][C:25]#[C:26][C:5]2[CH:6]=[CH:7][CH:8]=[C:3]([C:2]([F:1])([F:20])[F:21])[CH:4]=2)[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Participants

4

Reactant 2

HCID 745735-Phenyl-1-pentyneHCID 112439861-(Tosyloxy)-3-(trifluoromethyl)benzene

Product 1

HCID 252216091-(5-Phenyl-pent-1-ynyl)-3-trifluoromethyl-benzene

Reagents, catalysts & solvents 1

HCID 8900HeptaneSolvent

Procedure

This product was prepared from toluene-4-sulfonic acid 3-trifluoromethyl-phenyl ester and pent-4-ynyl-benzene following the general procedure for the Sonogashira cross-coupling process described above. Chromatography eluent: heptane; yield (140 mg, 97%); 1H NMR δ (CDCl3): 7.66 (s, 1H), 7.61-7.7.49 (m, 2H), 7.46-7.36 (m, 1H), 7.35-7.16 (m, 5H), 2.79 (t, J=7.15 Hz, 2H), 2.43 (t, J=7.20 Hz, 2H), 1.93 (p, J=7.11 Hz, 2H); LCMS m/z: 288.

Workup

  1. customyield (140 mg, 97%)

Sources & evidence

ORD record
ord-d565f91a5ef44e25ae2698ce2bedb337
Source dataset
uspto-grants-2013_07
Patent number
US08487109B2

Linked notes

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