Reaction #42177

Reaction equation

dicyclohexylamine

4-bromobenzaldehyde

trimethylsilylacetylene

sodium chloride

→

4-[(trimethylsilyl)ethynyl]benzaldehyde

Yield 88.0%

Solvents

tetrahydrofuran

toluene

tetrahydrofuran

Conditions

Workup

1. 1
   OtherA 50-ml four-necked flask was equipped with a stirrer
2. 2
   workup.ADDITIONadded into the flask
3. 3
   OtherThe flask was purged with argon
4. 4
   workup.STIRRINGby stirring at 30° C. for 30 minutes
5. 5
   workup.STIRRINGby stirring at 30° C. for 17 hours
6. 6
   workup.ADDITIONwere added
7. 7
   Otherfollowed by separation
8. 8
   OtherThe organic phase was purified by column chromatography

Procedure

A 50-ml four-necked flask was equipped with a stirrer, 20 a thermometer and a reflux condenser. 0.034 g (0.15 mmol) of palladium (II) acetate, 0.019 g (0.1 mmol) of copper (I) iodide, 1.088 g (6 mmol) of dicyclohexylamine and 9 ml of tetrahydrofuran were weighed in the flask, followed by stirring. Further, 0.174 g (0.3 mmol) of tri-tert-butylphosphonium tetra-para-tolylborate obtained in Example B-3 was weighed in air and added into the flask. The flask was purged with argon, followed by stirring at 30° C. for 30 minutes. 0.925 g (5 mmol) of 4-bromobenzaldehyde and 0.589 g (6 mmol) of trimethylsilylacetylene were added, followed by stirring at 30° C. for 17 hours. After the completion of the reaction, 10 ml of tetrahydrofuran, 5 ml of toluene and 15 ml of saturated sodium chloride solution were added, followed by separation. The organic phase was purified by column chromatography to afford 0.890 g of 4-[(trimethylsilyl)ethynyl]benzaldehyde (yield: 88 mol % based on 4-bromobenzaldehyde). The identification of the product was made by 1H-NMR and 13C-NMR.

Source