Dimethylformamide → HCID 86093855, compound

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The title compound was synthesized in analogy to 4-cyclopropyl benzaldehyde (described in example S53) using 310 mg of 4-bromo-2-chloro-1-(1-methoxy-1-methyl-ethyl)-benzene (1.18 mmol), 1.1 ml of a 1.6 molar solution of n-BuLi in hexane (1.76 mmol) and 457 μl of DMF (5.88 mmol). The isolated residue was purified by flash column chromatography (1:9 ether/pentane) to give 154 mg of 3-chloro-4-(1-methoxy-1-methyl-ethyl)-benzaldehyde (62%) as a colorless liquid. 1H NMR (CDCl3, 300 MHz): δ 1.69 (s, 6H), 3.18 (s, 3H), 7.69 (d, J=8.2 Hz, 1H), 7.75 (dd, J=8.2 and 1.7 Hz, 1H), 7.58 (d, J=1.7 Hz, 1H), 9.97 (s, 1H).

Provenance & Evidence