Butyl bromide → HCID 15812116, compound

Participants

Reaction Conditions

Reaction Steps

Into a dry 500 mL three-necked round-bottomed flask equipped with magnetic stirring bar and dropping funnel were placed 11.67 g (0.164 mol) of N-vinylformamide and 200 mL of anhydrous THF. The mixture was cooled to 15° C. in an ice bath under nitrogen and a total of 18.8 g (0.167 mol) of t-BuOK was added in three portions with constant stirring over 45 minutes. 1-Bromobutane, 24.5 g (0.179 mol) was then added to the reaction mixture dropwise over 30 minutes. When addition was complete, the reaction was allowed to warm to ambient temperature and stirred overnight. After potassium bromide salt was removed, the reaction mixture was concentrated under reduced pressure and diluted with 200 mL of water. The organic layer was extracted three times with diethyl ether. The combined organic layers were washed twice with water and dried over anhydrous magnesium sulfate. The resulting product was recovered after concentration in vacuum and purification by chromatography on silica (diethyl ether/petroleum ether (v/v=3:7). yield: 11.7 g (56%). IR (NaCl, v: cm−1): 1693 (—NHC(═O)H); 1630 (C═C). 1H-NMR (CDCl3, δ: ppm): 8.31, 8.14 (2s, 1H, —C(═O)H); 7.25–7.16, 6.61–6.52 (m, 1H, H2C═CH—); 4.62–4.45 (m, 1H, HaHbC═CH—); 4.43–(s, 1H, HaHbC═CH—); 3.60–3.45 (t, 2H, —NCH2CH2—); 1.61–1.54 (m, 2H, —CH2CH2CH2—); 1.40–1.32 (m, 2H, —CH2CH2CH3); 0.99–0.94 (t, 3H, —NCH2CH2CH2CH3).

Provenance & Evidence