Reaction #2487457

Reaction equation

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

cyclopropylboronic acid monohydrate

tricyclohexylphosphine

tripotassium phosphate monohydrate

→

title compound

Yield 86.5%

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

Yield 86.5%

Solvents

water

toluene

ethyl acetate

Conditions

Workup

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

Procedure

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