Triethylamine → 5-Chloro-4-(trifluoromethyl)-2-[(trimethylsilyl)ethynyl]aniline

HRID 1670739Notes

Reaction equation

Br[C:2]1[CH:8]=[C:7]([C:9]([F:12])([F:11])[F:10])[C:6]([Cl:13])=[CH:5][C:3]=1[NH2:4].[CH3:14][Si:15]([C:18]#[CH:19])([CH3:17])[CH3:16].C(N(CC)CC)C>C(OCC)C>[Cl:13][C:6]1[C:7]([C:9]([F:12])([F:11])[F:10])=[CH:8][C:2]([C:19]#[C:18][Si:15]([CH3:17])([CH3:16])[CH3:14])=[C:3]([CH:5]=1)[NH2:4]

Participants

Conditions

Temperature: 60 °C

Procedure

A mixture of 2-bromo-5-chloro-4-(trifluoromethyl)aniline (17.1 g), trimethylsilylacetylene (14.8 ml), bistriphenylphosphinepalladium dichloride (816 mg) and triethylamine (115 ml) was stirred at 60° C. for 9 hr. The reaction mixture was ice-cooled, diethyl ether was added and the mixture was filtered through a celite (trademark) filter. The filtrate was evaporated under reduced pressure to give a brown oil. The oil was purified by silica gel column chromatography (elution solvent:ethyl acetate-hexane (1:20-1:10)) to give 5-chloro-4-(trifluoromethyl)-2-[(trimethylsilyl)ethynyl]aniline (16.5 g, yield 92%).

Workup

temperaturecooled
filtrationthe mixture was filtered through a celite (trademark)
filtrationfilter
customThe filtrate was evaporated under reduced pressure
customto give a brown oil
customThe oil was purified by silica gel column chromatography (elution solvent:ethyl acetate-hexane (1:20-1:10))

Sources & evidence

ORD record: ord-475f1b59b2ce45ec9f90ae95bf1e2ff3
Source dataset: uspto-grants-2011_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07994196B2

Reaction notes

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