Dimethylformamide → 2,2-Dimethylbenzo[d][1,3]dioxole-5-carbaldehyde

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The title compound was synthesized in analogy to 4-cyclopropyl benzaldehyde (described in example S53) using 420 mg of 5-bromo-2,2-dimethyl-benzo[1,3]dioxole [CAS 73790-19-9] (1.83 mmol), 1.38 ml of a 1.6 molar solution of n-BuLi in hexane (2.20 mmol) and 712 μl of DMF (9.17 mmol). The isolated residue was purified by flash column chromatography (1:9 ether/pentane) to give 270 mg of 2,2-dimethyl-benzo[1,3]dioxole-5-carbaldehyde (83%) as a light yellow liquid. 1H NMR (CDCl3, 300 MHz): δ 1.72 (s, 6H), 6.84 (d, J=7.8 Hz, 1H), 7.26 (s, 1H), 7.87 (dd, J=8.0 and 1.7 Hz, 1H), 9.97 (s, 1H).

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