Dimethylformamide → 7-Bromo-2-tetralone

Participants

Reaction Steps

To a solution of (3-bromophenyl)acetic acid (˜10 g, 50 mmol) in 200 mL of DCM was added DMF (183 mg, 2.5 mmol) and then oxalyl dichloride (6.3 g, 50 mmol) was added dropwise over 30 min. The resulting mixture was stirred at room temperature for 6 hr and then concentrated under reduced pressure. A mixture of prepared acid chloride in 200 mL of DCM was added AlCl3 (13.2 g, 100 mmol) portion-wise at 0° C. After the mixture was stirred at 0° C. for 30 min, the solution was bubbled with ethene gas for 2 h and the resulting mixture was warmed to room temperature and stirred overnight. Then 300 mL of water was added dropwise over 30 min with stirring. Then separated the organic layer and extracted the aqueous layer with 200 mL of DCM. The combined organic layers were washed with 1N HCl (200 mL), saturated NaHCO3 (200 mL) and brine (200 mL) and then dried over Na2SO4. Then the organic layer was concentrated under reduced pressure to remove the solvent. The crude product was purified via chromatography (EtOAc/petrol ether 1:20 to 1:5) to give the desired 7-bromo-3,4-dihydronaphthalen-2(1H)-one along with the isomeric side product 5-bromo-3,4-dihydronaphthalen-2(1/1)-one. 1H-NMR (400 MHz, CDCl3) δ 7.33 (d, J=8.0 Hz, 1H), 7.27 (s, 1H), 7.10 (d, J=8.0 Hz, 1H), 3.01 (t, J=6.8 Hz, 2H), 2.54 (t, J=6.8 Hz, 2H); MS m/e 225 (M+1)+.

Provenance & Evidence