Reacción #159272

Ecuación de reacción

4-iodotoluene

triethylamine

1,2-Dimethoxyethane n-butanol

→

butyl 4-methylbenzoate

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroThe reaction vessel was evacuated
2. 2
   Otropurged with carbon monoxide (CO)
3. 3
   Temperaturato cool to room temperature
4. 4
   workup.ADDITIONdiluted with dichloromethane (50 mL)
5. 5
   Filtraciónfiltered through a polyethylene frit (20-micron porosity)
6. 6
   LavadoThe filtrate was washed with water (2×20 mL)
7. 7
   Secadodried (MgSO4)
8. 8
   OtroEvaporation
9. 9
   Otrounder reduced pressure and purification by column chromatography

Procedimiento

Microencapsulated Pd(OAc)2 (prepared as described in Example 1, 0.23 g, 2 mol %, based on palladium content) was added to a solution of 4-iodotoluene (1 mmol) and triethylamine (4 mmol) in 1,2-Dimethoxyethane/n-butanol (1:1, 10 mL). The reaction vessel was evacuated and purged with carbon monoxide (CO). The reaction mixture was stirred at 95° C. for 24 h under a CO atmosphere (using a balloon). The mixture was allowed to cool to room temperature, diluted with dichloromethane (50 mL) and filtered through a polyethylene frit (20-micron porosity). The filtrate was washed with water (2×20 mL) and dried (MgSO4). Evaporation under reduced pressure and purification by column chromatography gave butyl 4-methylbenzoate, 89%; IR: 1714; 1H NMR (400 MHz; CDCl3): 7.93 (2H, d, J 8.2), 7.23 (2H, d, J 8), 4.31 (2H, t, J 6.6), 2.41 (3H, s), 1.78-1.71 (2H, m), 1.49 (2H, sext, J 7.5) and 0.98 (3H, t, J 7.4); 13C NMR (CDCl3): 167.2, 143.8, 130.0, 129.4, 128.2, 65.0, 31.2, 22.0, 19.7 and 14.1.

Fuente