2,6-Lutidine → (E)-(2-bromomethyl-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-ylidene)acetonitrile

Participants

Reaction Steps

(E)-(2-Hydroxymethyl-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-ylidene)acetonitrile (JP-B-2526005; 10.00 g, 38.3 mmol) was dissolved in THF (380 mL), 2,6-lutidine (26.7 mL, 230 mmol), lithium bromide (19.94 g, 230 mmol) and methanesulfonic anhydride (16.67 g, 95.7 mmol) were added, and the mixture was stirred at room temperature for 16 hr. Ethyl acetate was added to the mixture, and the organic layer was washed with brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to give a residue. Ethyl acetate (10 mL) and hexane (5 mL) were added to the residue, and the mixture was filtered to give the title compound (9.18 g, 74%).

Provenance & Evidence