Water → 6-Cyanoindane-4-carboxylic acid

Participants

Reaction Conditions

Reaction Steps

In a flask designed for high pressure (max. 12 bar) 7-bromoindane-5-carbonitrile (1.18 g, 5.3 mmol) was mixed with DMF (50 mL), bis(triphenylphosphine)palladium(II) chloride (0.1 g, 0.14 mmol), triphenylphosphine (0.1 g, 0.38 mmol), triethylamine (1.0 g, 9.9 mmol) and water (5 mL). While stirring the flask was alternately evacuated and then loaded with carbon monoxide. The procedure was repeated 4 times and then carbon monoxide was introduced until a pressure of 6 bar was obtained. The reaction mixture was heated to 90° C. for 60 h and then cooled to room temperature. The content was transferred to a beaker by means of ether (100 mL) and water (200 mL). The organic layer was separated off and precipitated Pd was removed by decantation. The aqueous layer was acidified with conc. HCl and then extracted thrice with ether (50 mL). The combined organic solutions were washed with brine, dried over Na2SO4 and the solvent was evaporated. The solid residue was treated with cold CH2Cl2, then filtrated off and then dried. There was obtained 0.6 g (60%) of 6-cyanoindane-4-carboxylic acid as a solid material. 1H NMR (300 MHz, CDCl3): 2.1-2.2 (q, 2H), 3.0 (t, 2H), 3.4 (t, 2H), 7.7 (s, 1H), 8.2 (s, 1H).

Provenance & Evidence