Sodium Hydroxide → 7-Bromoindane-5-carboxylic acid

Temperature

50 °C

1-(7-bromo-2,3-dihydro-1H-inden-5-yl)ethanone (8.6 g, 36 mmol) was dissolved in dimethoxyethane (100 mL) and to the solution were added NaClO aq (200 mL 1M, 200 mmol) and NaOH aq (20 mL 10 M, 200 mmol). The mixture was heated to 50° C. for 1 h and then diluted with water (200 mL). Sodium pyrosulfite (5.7 g, 30 mmol) was added. The mixture was washed with ether, acidified with concentrated HCl and then extracted twice with ether (150 mL). The organic solution was washed with brine, dried and then the solvent was evaporated. The solid residue was treated with cold CH2Cl2 (−40° C.), then filtered off and dried. There was obtained 7.1 g (82%) of 7-bromoindane-5-carboxylic acid as a solid material. 1H NMR (300 MHz, CD3OD): 2.0-2.2 (q, 2H), 2.9 (t, 2H), 3.1 (t, 2H), 7.8 (s, 1H), 7.9 (s, 1H).

1. washThe mixture was washed with ether
2. extractionextracted twice with ether (150 mL)
3. washThe organic solution was washed with brine
4. customdried
5. customthe solvent was evaporated
6. additionThe solid residue was treated with cold CH2Cl2 (−40° C.)
7. filtrationfiltered off
8. customdried

ORD record

ord-f5bdfcf65e2d4422b1794e579a2b1cf0

Source dataset

uspto-grants-2008_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07402581B2