4-Ethynyl-1,2-dimethoxybenzene → 1,2-Dimethoxy-4-(4-Trifluoromethoxy-phenylethynyl)-benzene

HRID 451274Notes

Reaction equation

HRID 451274 reaction equation
[F:1][C:2]([F:22])([F:21])[O:3][C:4]1[CH:9]=[CH:8][C:7](OS(C2C=CC(C)=CC=2)(=O)=O)=[CH:6][CH:5]=1.[C:23]([C:25]1[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[C:27]([O:33][CH3:34])[CH:26]=1)#[CH:24]>CCCCCCC>[CH3:32][O:31][C:28]1[CH:29]=[CH:30][C:25]([C:23]#[C:24][C:7]2[CH:6]=[CH:5][C:4]([O:3][C:2]([F:1])([F:21])[F:22])=[CH:9][CH:8]=2)=[CH:26][C:27]=1[O:33][CH3:34]

Participants

4

Reactant 2

HCID 36164214-Ethynyl-1,2-dimethoxybenzeneHCID 18424495Toluene-4-sulfonic acid 4-trifluoromethoxy-phenyl ester

Product 1

HCID 252217261,2-Dimethoxy-4-(4-Trifluoromethoxy-phenylethynyl)-benzene

Reagents, catalysts & solvents 1

HCID 8900HeptaneSolvent

Procedure

This product was prepared from toluene-4-sulfonic acid 4-trifluoromethoxy-phenyl ester and 4-ethynyl-1,2-dimethoxy-benzene following the general procedure for the Sonogashira cross-coupling process described above. Chromatography eluent: heptane; yield (140 mg, 87%); 1H NMR δ (CDCl3): 7.52 (d, J=8.40 Hz, 2H), 7.21-7.16 (m, 3H), 6.83 (d, J=8.41 Hz, 2H), 3.85 (s, 6H); LCMS m/z: 322.

Workup

  1. customyield (140 mg, 87%)

Sources & evidence

ORD record
ord-b6bdbb5fef8240af92024e3d936b11b2
Source dataset
uspto-grants-2013_07
Patent number
US08487109B2

Reaction notes

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