Hydrochloric Acid → 1-Indanone, 6-bromo-

Temperature

40 °C

3-(4-Bromophenyl)propionyl chloride (36.9 g, 0.15 mol) was dissolved in 300 mL DCM and AlCl3 (23.76 g, 0.18 mol) was added slowly. At the completion of the reaction, the mixture was heated to 40° C. and refluxed for 90 minutes and then poured onto ice. Dilute HCl aqueous solution was added and the mixture was extracted with diethyl ether. The organic layer was washed with 2M HCl aqueous solution, water and brine. The product was purified by column chromatography on silica gel eluting with PE:EA (20:1) to obtain a pale brown solid. After removing solvent under vacuum, 23 g (75%) of the desired product 6-bromo-2,3-dihydro-1H-inden-1-one (1B): 1H NMR (DMSO-d6, 400 MHz) δ2.6 (m, 2H), 3.1 (m, 2H), 7.55 (m, 1H), 7.1 (m, 1H), 7.85 (m, 1H).

1. customAt the completion of the reaction
2. temperaturerefluxed for 90 minutes
3. additionpoured onto ice
4. extractionthe mixture was extracted with diethyl ether
5. washThe organic layer was washed with 2M HCl aqueous solution, water and brine
6. customThe product was purified by column chromatography on silica gel eluting with PE
7. customEA (20:1) to obtain a pale brown solid
8. customAfter removing solvent under vacuum, 23 g (75%) of the desired product 6-bromo-2,3-dihydro-1H-inden-1-one (1B)

ORD record

ord-7eea2bba99324cf7831ea0c7ae60083a

Source dataset

uspto-grants-2012_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08114893B2