Toluene → HCID 66938969, compound

Participants

Reaction Conditions

Reaction Steps

Combine 1,3-dibromo-5-fluorobenzene (5.0 g, 19.7 mmol), 1-methyl-4-(methylamino)piperidine (2.58 mL, 17.7 mmol), 2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (0.49 g, 0.79 mmol), sodium t-butoxide (2.57 g, 27.58 mmole) and toluene (100 mL), stir and heat at 80° C. After 10 minutes, add Pd2(dba)3 (0.49 g, 0.79 mmol). After 3 hr. at 80° C., cool to ambient temperature. Dilute with ethyl acetate (100 mL) and wash with water (50 mL). Dry the organic layer over sodium sulfate, filter, and concentrate to an oil. Purify the residue by silica gel flash chromatography eluting with 10% (2M NH3-methanol) in CH2Cl2 to obtain 2.95 g (55%)of the title intermediate: 1H NMR (CDCl3): 6.6 (s, 1H), 6.5 (m, 1H), 6.3 (m, 1H), 3.5 (m, 1H), 2.9 (m, 2H), 2.7 (s, 3H), 2.3 (s, 3H), 2.0 (m, 2H), 1.8 (m, 2H), 1.7 (m, 2H).

Provenance & Evidence