Benzene → HCID 21692926, compound

Participants

Reaction Steps

In an oven dried flask was added 4-bromo-3-fluorobenzoic acid (1.0 g, 0.0046 mol), thionyl chloride (0.65 mL, 0.0089 mol) and a drop of DMF and the reaction was refluxed for 2 h. The thionyl chloride was then distilled off and benzene (20 mL, 0.2 mol) and aluminum trichloride (0.576 g, 0.00432 mol) was added to the reaction mixture and the reaction 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=7.45-7.55 (m, 3H), 7.58 (dd, J=8.84, 1.77 Hz, 1H), 7.60-7.66 (m, 1H), 7.70 (dd, J=8.21, 6.69 Hz, 1H), 7.75-7.82 (m, 2H).

Provenance & Evidence