Benzene → 684271-17-8

Participants

Reaction Steps

In an oven dried flask was added 2-fluoro-4-bromobenzoic acid (1.0 g, 0.0046 mol), thionyl chloride (0.77 mL, 0.010 mol) and a drop of DMF and the reaction was refluxed for 2 h. The excess thionyl chloride was then distilled off and the residual thionyl chloride was removed on the high vacuum pump. Benzene (20 mL, 0.2 mol) and aluminum trichloride (0.676 g, 0.00507 mol) were added to the reaction mixture. The reaction mixture was stirred at room temp for 1 h. The crude reaction mixture was poured onto ice and conc. HCl (15 mL). The organic layer was separated and the aqueous layer extracted with EtOAc. The combined organic phases were washed with 5% aq NaOH solution, water and dried (Na2SO4). The organic phase was concentrated in vacuo to give a residue which was purified by silica gel chromatography, eluting with 2% EtOAc in hexane. 1H NMR (400 MHz, CDCl3): δ=7.32-7:41 (m, 1H), 7.42-7.53 (m, 4H), 7.56-7.67 (m, 1H), 7.77-7.88 (m, 2H). MS (ES+): m/z 280.78 (40) [MH+]. HPLC: tR=3.8 min(Open Lynx polar—5 min).

Provenance & Evidence