4-Nitrobenzoyl chloride → 4-Nitrobenzaldehyde

Participants

Reaction Conditions

Reaction Steps

AlCl3 (101 mg, 0.757 mmol) was weighed quickly into an argon-flushed vial. While the vial was being purged with argon, dichloroethane was added slowly. The ensuing mixture was syringed quickly into a round-bottom flask and cooled to 0° C. A solution of 4-nitro benzoyl chloride (70 mg, 0.377 mmol) in dichloroethane was added slowly into the suspension of AlCl3 at O—C. This mixture was stirred at 0° C. for 30 min after which a fresh solution of compound 6 (64 mg, 0.253 mmol) in dichloroethane was added slowly to the reaction mixture being stirred at 0° C. After the reaction was stirred at 0° C. for 30 min, it was brought to room temperature and then stirred for another 30 min. The reaction was quenched by adding ice-cold water slowly. The organic layer was extracted into dichloromethane and washed with water and brine, dried with MgSO4 and purified using flash chromatography (ethyl acetate and hexane). The purified material was dried down into a brown/orange solid. Yield: 45 mg, 44%. 1H NMR (400 MHz, CDCl3) δ 8.63 (d, J=9.84 Hz, 1H), 8.44 (d, J=9.89 Hz, 1H), 8.29 (d, J=8.82 Hz, 2H), 7.86 (d, J=8.81 Hz, 2H), 7.71 (t, J=9.82 Hz, 1H), 7.46 (t, J=9.72 Hz, 1H), 7.29 (t, J=9.93 Hz, 1H), 6.67 (s, 1H), 4.70 (s, 2H), 2.42 (s, 3H), 2.39 (s, 3H); 13C NMR (100 MHz, CDCl3) δ 192.2, 170.3, 152.3, 150.4, 149.5, 146.3, 141.4, 140.2, 138.2, 135.6, 133.7, 130.2, 127.2, 125.0, 124.3, 123.6, 123.3, 113.2, 29.0, 16.9. HRMS (ES) calcd MH+ [C23H19N2O3S]+403.1038. found 403.1106.

Provenance & Evidence