Reacción #2487457

Ecuación de reacción

tert-butyl (4-iodo-2-methylphenyl)carbamate

cyclopropylboronic acid monohydrate

tricyclohexylphosphine

tripotassium phosphate monohydrate

→

title compound

Rendimiento 86.5%

tert-Butyl (4-cyclopropyl-2-methylphenyl)carbamate

Rendimiento 86.5%

Disolventes

water

toluene

ethyl acetate

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.WAITThe reaction mixture was left
2. 2
   Temperaturato cool
3. 3
   Filtraciónfiltered through Celite (registered trademark)
4. 4
   LavadoThe filtrate was washed with brine
5. 5
   Secadodried over anhydrous sodium sulfate
6. 6
   Concentraciónconcentrated under reduced pressure
7. 7
   OtroThe residue was purified by silica gel column chromatography (eluting solvent: ethyl acetate-hexane)

Procedimiento

A mixture of tert-butyl (4-iodo-2-methylphenyl)carbamate (1.04 g), cyclopropylboronic acid monohydrate (422 mg), palladium(II) acetate (35.1 mg), tricyclohexylphosphine (87.5 mg), tripotassium phosphate monohydrate (2.52 g), toluene (8.7 mL), and water (0.87 mL) was stirred at 100° C. for 15 hours. The reaction mixture was left to cool and then diluted with ethyl acetate and filtered through Celite (registered trademark). The filtrate was washed with brine and dried over anhydrous sodium sulfate, and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluting solvent: ethyl acetate-hexane) to obtain the title compound (668 mg). 1H-NMR (CDCl3) δ ppm: 0.55-0.70 (2H, m), 0.80-1.00 (2H, m), 1.51 (9H, s), 1.75-1.90 (1H, m), 2.21 (3H, s), 5.85-6.45 (1H, br), 6.75-7.00 (2H, m), 7.45-7.75 (1H, m).

Fuente