반응 #2487457

반응 방정식

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

cyclopropylboronic acid monohydrate

tricyclohexylphosphine

tripotassium phosphate monohydrate

→

title compound

수율 86.5%

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

수율 86.5%

용매

water

toluene

ethyl acetate

반응 조건

후처리

1. 1
   workup.WAITThe reaction mixture was left
2. 2
   온도to cool
3. 3
   여과filtered through Celite (registered trademark)
4. 4
   세척The filtrate was washed with brine
5. 5
   건조dried over anhydrous sodium sulfate
6. 6
   농축concentrated under reduced pressure
7. 7
   기타The residue was purified by silica gel column chromatography (eluting solvent: ethyl acetate-hexane)

실험 절차

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).

출처