Benzene → (4-Bromo-3-methoxyphenyl)-phenylmethanone

In an oven dried flask was added 4-bromo-3-methoxybenzoic acid (1.00 g, 4.33 mmol), 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 oh the pump. Benzene (20 mL, 0.2 mol) and aluminum trichloride (0.676 g, 5.07 mmol) were added to the reaction mixture. The reaction mixture turned yellow in color on addition of AlCl3. 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.

1. customIn an oven dried flask
2. distillationThe excess thionyl chloride was then distilled off
3. customthe residual thionyl chloride was removed oh the pump
4. customThe crude reaction mixture
5. customThe organic layer was separated
6. extractionthe aqueous layer extracted with EtOAc
7. washThe combined organic phases were washed with 5% aq NaOH solution, water
8. dry with materialdried (Na2SO4)
9. concentrationThe organic phase was concentrated in vacuo
10. customto give a residue which
11. customwas purified by silica gel chromatography
12. washeluting with 2% EtOAc in hexane

ORD record

ord-3ed3fb5275944e52ad5d293aff3b558e

Source dataset

uspto-grants-2013_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08481733B2