Allyl iodide → HCID 22177261, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of (3,5-dichloro-phenyl)-carbamic acid-tert-butyl ester (6 g, 22.89 mmol) in DMF (130 mL) at 0° C. under Ar was added NaH (60% dispersion in mineral oil, 1.725 g, 45 mmol, 2 eq). The mixture was stirred at 0° C. for 30 min and then allyl iodide (13.32 mL, 110 mmol, 5 eq) was added over 5 min. The mixture was warmed to room temperature and stirred for 2 h. The mixture was then diluted with EtOAc (200 mL) and washed with saturated aqueous NaHCO3 (200 mL). The aqueous phase was washed with EtOAc (3×60 mL) and the combined organic extracts were washed with saturated aqueous NaCl (200 mL), dried over Na2SO4, filtered and concentrated to give a brown oil which was purified by flash column chromatography eluting with 2% EtOAc/hexanes to give allyl(3,5-dichloro-phenyl)-carbamic acid-tert-butyl ester as a clear oil (4.632 g, 15.33 mmol, 67%).). 1H NMR (300 MHz, CDCl3): δ 7.41 (s, 1H), 7.24 (m, 2H), 6.00 (m, 1H), 5.30 (m, 2H), 4.30 (m, 2H), 1.59 (s, 9H).

Provenance & Evidence