1,3-Dimethoxybenzene → HCID 178492411, compound

Participants

Reaction Steps

Diazonium salt 1 (9.8 mg, 0.030 mmol) in 1 mL of 95% aqueous ethanol was added to a solution of 1,3-dimethoxybenzene (8.7 mg, 0.063 mmol) in 0.5 mL of 95% aqueous ethanol. After 2 weeks, the solvent was evaporated to give a red oil, whose purification by SiO2 column chromatography (1:1 hexane/CH2Cl2) afforded 27a as orange crystals (10.8 mg, 98%); m.p. 88.0-88.5° C. IR (ATR): {tilde over (v)}=2943, 1600, 1496, 1471, 1294, 1253, 1211, 767 cm−1. MS (GC, EI): m/z=368 [M+], 241 [M+-SF5], 165 [M+-C6H4SF5]. 1H NMR (500 MHz, CDCl3): δ=7.89 (d, J=9.0 Hz, 2H), 7.86 (d, J=9.0 Hz, 2H), 7.78 (d, J=9.0 Hz, 1H), 6.60 (d, J=2.4 Hz, 1H), 6.56 (dd, J=9.0, 2.4 Hz, 1H), 4.03 (s, 3H), 3.91 (s, 3H) ppm. 13C NMR (125 MHz, CDCl3): δ=164.8 (C), 159.5 (C), 154.4 (C), 154.1 (C), 136.7 (C), 126.9 (2CH), 122.5 (2CH), 118.2 (CH), 105.9 (CH), 98.9 (CH), 56.3 (CH3), 55.7 (CH3) ppm. 19F NMR (470 MHz, CDCl3): δ=84.3 (quint, J=150 Hz, 1 F), 63.2 (d, J=150 Hz, 4 F) ppm.

Provenance & Evidence