4-(Bromomethyl)-1,2-difluorobenzene → HCID 53258398, compound

Participants

Reaction Steps

The 11-(methylthio)-9H-benzo[b]pyrimido[5,4-f]tetrazolo[1,5-d][1,4]diazepine (5) (1.03 g) in DMF (20 mL) was treated with 1.1 eq. of 1M t-BuOK in t-BuOH (4 mL). The mixture was stirred at R.T. for 10 minutes then the 3,4-difluorobenzyl bromide (0.6 mL) was added. The mixture was stirred at R.T. for one hour. The reaction mixture was quenched with the addition of saturated aqueous ammonium chloride solution (20 mL). The mixture was extracted with ethyl acetate (3×50 mL) and the combined organic extracts were dried over sodium sulfate. Concentration in vacuo provided the titled product as a yellow solid (6) (1.3 g). M.p.=281-283° C.; 400 MHz 1H NMR (DMSO-d6) δ: 8.91 (s, 1H), 7.79 (dd, J=8.4, 1.6 Hz, 1H), 7.61 (dd, J=8.4, 1.2 Hz, 1H), 7.54 (ddd, J=8.8, 7.2, 1.6 Hz, 1H), 7.45-7.34 (m, 2H), 7.32-7.25 (m, 1H), 7.17-7.13 (m, 1H), 5.24 (s, 2H), 2.56 (s, 3H); LCMS [M+H]: 410; Calc. for C19H13F2N7S: C, 55.74; H, 3.20; N, 23.95; found C, 55.65; H, 2.96; N, 23.67.

Provenance & Evidence