1-Bromo-3-ethynylbenzene → 4-[(3-bromophenyl)ethynyl]-1-(2,2,2-trifluoroethyl)-1H-pyrazole

HRID 646231Notes

Reaction equation

I[C:2]1[CH:3]=[N:4][N:5]([CH2:7][C:8]([F:11])([F:10])[F:9])[CH:6]=1.[Br:12][C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([C:19]#[CH:20])[CH:14]=1>C(N(CC)CC)C.C(#N)C.[Cu](I)I>[Br:12][C:13]1[CH:14]=[C:15]([C:19]#[C:20][C:2]2[CH:3]=[N:4][N:5]([CH2:7][C:8]([F:11])([F:10])[F:9])[CH:6]=2)[CH:16]=[CH:17][CH:18]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of 4-iodo-1-(2,2,2-trifluoroethyl)-1H-pyrazole (4.14 g, 15 mmol) in triethylamine (53 mL) is added tetrakis(triphenylphosphine)paddadium (1.20 g, 1.04 mmol), copper iodide (0.28 g, 1.46 mmol) and a solution of 1-bromo-3-ethynylbenzene (2.78 g, 15 mmol) in acetonitrile (15 mL) at room temperature. After heating for 1 hour at 80° C., the reaction mixture is cooled and concentrated. The crude material is purified by chromatography (silica gel, EtOAc/hexane:5/95) to give the title compound as a solid (4.91 g, 99%). mp: 107-109° C. MS (+) EI: 328 M+.

Workup

customat room temperature
temperaturethe reaction mixture is cooled
concentrationconcentrated
customThe crude material is purified by chromatography (silica gel, EtOAc/hexane:5/95)

Sources & evidence

ORD record: ord-2c758ef124dd43aab1026fa2204a173e
Source dataset: uspto-grants-2010_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07705030B2

Reaction notes

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