1-Bromo-4-iodobenzene → (4-Bromophenylethynyl)trimethylsilane
Reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5](I)=[CH:4][CH:3]=1.[CH3:9][Si:10]([C:13]#[CH:14])([CH3:12])[CH3:11]>>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:14]#[C:13][Si:10]([CH3:12])([CH3:11])[CH3:9])=[CH:4][CH:3]=1Participants
Procedure
1-bromo-4-iodobenzene was reacted with trimethylsilylacetylene via Sonogashira coupling reaction under the PdCl2(PPh3)2/CuI/TEA catalyst system to produce (4-bromophenylethynyl)trimethylsilane as a white solid, quantitatively. Specifically, 11.32 g (40 mmol) of 1-bromo-4-iodobenzene was placed in a round bottomed flask equipped with a septum and a stirring bar. The flask was put into a glove box and 281 mg (0.4 mmol) of dichlorobis-(triphenylphosphine)palladium(II) and 19 mg (0.1 mmol) of CuI were added. Afterward, 100 mL of dried triethylamine and 5.65 mL (40 mmol) of trimethylsilylacetylene were injected into the flask through syringes while stirring. The mixture was stirred at room temperature for 2 h. Precipitates were formed. The precipitates were filtered and washed with diethyl ether. The solutions were combined and the solvent was evaporated. The crude product was purified by a silica gel column chromatography using hexane as eluent. A white powdery product was obtained in 97% yield (9.82 g).
Sources & evidence
- ORD record
- ord-1ddcdaed87974d1aa96a309f29a74a29
- Source dataset
- uspto-grants-2015_12
- Patent number
- US09200121B2
Reaction notes
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