2,6-Lutidine → 1-Propene, 3-bromo-2-[(1,1-dimethylethyl)sulfonyl]-

Participants

Reaction Steps

A mixture of 16.78 g (0.052 mol) of 1,3-dibromo-2-(t-butylsulfonyl) propane and 14 mL (0.12 mol) of 2,6-lutidine in 55 mL of CH2Cl2 was refluxed for 75 minutes. The solution was allowed to cool to room temperature and extracted with three 80-mL portions of 5% HCl followed by 80 mL of water. The organic layer was dried over MgSO4, filtered, and the solvent removed in vacuo from a water bath at 45° C. to give 11.46 g (91%) of the allyl bromide as a white solid, mp 40.5°14 42.0° C., which was used without further purification; IR (KBr) 2980 cm-1, 1480, 1395, 1230, 1100, 970, 730, 640; 1H NMR (CDCl3) δ1.40 (s, 9H, t-butyl), 4.30 (s, 2H CH2Br), 6.50 (s, 2H, vinyl).

Provenance & Evidence