Dimethylformamide → 3-Chloro-4-(1-methylcyclopropyl)-benzaldehyde

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The title compound was synthesized in analogy to 4-cyclopropyl benzaldehyde (described in example S53) using 4-bromo-2-chloro-1-(1-methylcyclopropyl)-benzene (350 mg, 1.43 mmol), n-BuLi (980 μl, 1.6M solution in hexane, 1.57 mmol) and DMF (443 μl, 5.70 mmol). The isolated residue was purified by flash column chromatography (1:9 ether:pentane) to give 3-chloro-4-(1-methylcyclopropyl)-benzaldehyde (176 mg, 63%) as a colorless oil. 1H NMR (CDCl3, 300 MHz): δ 9.94 (s, 1H), 7.84 (d, J=1.5 Hz, 1H), 7.69 (dd, J=1.5, 8.0 Hz, 1H), 7.52 (d, J=8.0 Hz, 1H), 1.38 (s, 3H), 0.90-0.80(m, 4H).

Provenance & Evidence