Benzyl Bromide → HCID 59685145, compound

Participants

Reaction Steps

Dissolve preparation 2 (66.5 g, 275.89 mmol) in 1.5 L of dry DMF. Add finely powdered (325 mesh) K2CO3 (91.56 g, 662.13 mmol) followed by benzyl bromide (56.63 g, 331.07 mmol). Stir rapidly at room temperature overnight. Add 2 L of EtOAc, wash with H2O (1×2 L), 10% LiCl (3×, 4 L total volume) and brine. Dry over Na2SO4, filter and civ to yield a brown solid. Dissolve in hot EtOAc (2 L), filter off an insoluble brown solid, add hexane (˜500 mL) and allow to cool slowly, overnight. Filter off the resultant brown solid. This yields 50.3 g of a dark brown material. A second crop crashes out of the filtrate. This yields 8.1 g of a tan solid. Reduce the filtrate volume to ˜500 mL and placed on a plug of silica gel (1 kg, eluted with 1:1 EtOAc/hexane) to yield an additional 14.9 g of a darker brown solid. The total combined yield is 73.3 g (80%) of preparation 3. NMR (DMSO-d6) δ 7.96 (d, J=9.2 Hz, 1H), 7.58 (d, J=2.6 Hz, 1H), 7.45-7.32 (m, 6H), 6.53 (d, J=9.7 Hz, 1H), 5.15 (s, 2H).

Provenance & Evidence