Réaction #2487457

Équation de réaction

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

cyclopropylboronic acid monohydrate

tricyclohexylphosphine

tripotassium phosphate monohydrate

→

title compound

Rendement 86.5%

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

Rendement 86.5%

Solvants

water

toluene

ethyl acetate

Conditions de réaction

Traitement

1. 1
   workup.WAITThe reaction mixture was left
2. 2
   Températureto cool
3. 3
   Filtrationfiltered through Celite (registered trademark)
4. 4
   LavageThe filtrate was washed with brine
5. 5
   Séchagedried over anhydrous sodium sulfate
6. 6
   Concentrationconcentrated under reduced pressure
7. 7
   AutreThe residue was purified by silica gel column chromatography (eluting solvent: ethyl acetate-hexane)

Mode opératoire

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).

Source