Hydrochloric Acid → HCID 22173403, compound

Temperature

52.5 °C

94.37 g (0.40 mol) 1,4-Dibromobenzene and 106.7 g (0.80 mol) anhydrous aluminum trichloride were placed in a 1000 ml round bottom flask equipped with a mechanical stirrer. 62.72 g (0.60 mol) 2-Methyl-acryloyl chloride were added under heat evolution (50-55° C.). The mixture was heated, starting at 105° C. a strong gas evolution was observed and the temperature rose to 135° C. Heating of the now solid mass was continued for 3 h at 110° C. After cooling to room temperature 200 g ice was added very carefully, followed by the careful addition of 200 ml cone. HCl. The mixture was extracted three times with 250 ml dichloromethane each. The combined organic layers were washed with 250 ml water and 250 ml of a saturated sodium bicarbonate solution, dried over magnesium sulfate, and the solvent was removed in vacuo. Flash chromatography using silica and heptane/dichloromethane (1:2) yielded 19.3 g (63 mmol, 16%) of the desired indanone as a white solid. 1H-NMR (500 MHz, CDCl3): δ=7.67, 7.54 (2×d, 2H, aromatic), 3.30 (m, 1H, COCHCH3), 2.74-2.64 (m, 2H, benzylic), 1.30 (d, 3H, CH3) ppm.

1. customequipped with a mechanical stirrer
2. temperatureThe mixture was heated
3. customstarting at 105° C.
4. customrose to 135° C
5. temperatureHeating of the now solid mass
6. additionwas added very carefully
7. additionfollowed by the careful addition of 200 ml cone
8. extractionThe mixture was extracted three times with 250 ml dichloromethane each
9. washThe combined organic layers were washed with 250 ml water and 250 ml of a saturated sodium bicarbonate solution
10. dry with materialdried over magnesium sulfate
11. customthe solvent was removed in vacuo

ORD record

ord-6ee24eddfd8d43d18ddccc12cc97f17c

Source dataset

uspto-grants-2012_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08168556B2