4-Ethynylaniline → 4-(4-Trifluoromethoxy-phenylethynyl)-phenylamine

HRID 451275Notes

Reaction equation

HRID 451275 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]([NH2:31])=[CH:27][CH:26]=1)#[CH:24]>CCCCCCC>[F:22][C:2]([F:1])([F:21])[O:3][C:4]1[CH:5]=[CH:6][C:7]([C:24]#[C:23][C:25]2[CH:30]=[CH:29][C:28]([NH2:31])=[CH:27][CH:26]=2)=[CH:8][CH:9]=1

Participants

4

Reactant 2

HCID 37600254-EthynylanilineHCID 18424495Toluene-4-sulfonic acid 4-trifluoromethoxy-phenyl ester

Product 1

HCID 252217274-(4-Trifluoromethoxy-phenylethynyl)-phenylamine

Reagents, catalysts & solvents 1

HCID 8900HeptaneSolvent

Procedure

This product was prepared from toluene-4-sulfonic acid 4-trifluoromethoxy-phenyl ester and 4-ethynyl-phenylamine. Chromatography eluent: heptane; yield (111 mg, 80%); 1H NMR δ (CDCl3): 7.5 (d, J=8.42 Hz, 2H), 7.33 (d, J=8.60 Hz, 2H), 7.18 (d, J=8.41 Hz, 2H), 6.62 (d, J=8.62 Hz, 2H), 3.82 (s, 2H); LCMS m/z 277.

Workup

  1. customyield (111 mg, 80%)

Sources & evidence

ORD record
ord-446b487ddeb148afb40c713e34567c8d
Source dataset
uspto-grants-2013_07
Patent number
US08487109B2

Reaction notes

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