1,3-Dibromobenzene → HCID 58345149, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 1,3-dibromobenzene (472 mg, 2 mmol) in toluene (5 mL), were added azetidine hydrochloride (187 mg, 2 mmol), tris(dibenzylideneacetone)dipalladium (46 mg, 0.05 mmol), racemic BINAP (93 mg, 0.15 mmol) and sodium tert-butoxyde (230 mg, 2.4 mmol). The reaction was heated to 80° C. for 12 hr under nitrogen gas. The reaction mixture was filtered through celite and the filtered mixture was evaporated. The residue was purified by silica gel column chromatography (hexane:ethyl acetate: methanol=10:0:0 to 9:1:0.1) gave the product (51 mg, 12%). 400 M Hz 1H-NMR (CDCl3) δ: 7.04 (t, J=8.0 Hz, 1H), 6.82 (dd, J=8.0 Hz and 1.1 Hz, 1H), 6.55 (t, J=2.0 Hz, 1H), 6.33 (dd, J=7.7 Hz and 2.0 Hz, 1H), 3.87 (t, J=7.2 Hz, 4H), 2.40-2.34 (m, 2H); LCMS: 212[M+H].

Provenance & Evidence