2-Vinylpyridine → HCID 54062802, compound

Participants

Reaction Steps

124.4 g (417.8 mmol) of 2-Bromo-4-chlorobenzyloxybenzene, 54.8 ml (501.4 mmol) of 2-vinylpyridine, 4.69 g (20.9 mmol) palladium acetate, 25.4 g (83.6 mmol) tritolylphosphine, and 48 g (584.9 mmol) sodium acetate are heated together in 200 ml DMF at 165° C. (oil bath temperature) under nitrogen for 8 hours. The cooled mixture is evaporated to dryness in vacuo. The residue is then diluted with Et2O:DCM (3:1, 1 L) and washed with sodium carbonate solution (1M, 3×1 L). The aqueous washings are extracted with Et2O:DCM (3:1, 1L) and the combined organic extract dried using MgSO4, filtered through celite, and evaporated to dryness to leave an orange solid. Flash chromatography (SiO2, DCM:pentane 3:1) gave a yellow solid which was triturated with pentane (600 ml) to give the title compound as a pale yellow solid (77.5 g, 58%), m.p. 105.2-105.8° C. 6H (250 MHz, CDCl3) 8.60 (d, J=4.5 Hz, 1H), 7.96 (d, J=16.3 Hz, 1H), 7.64-7.60 (m, 2H), 7.46-7.34 (m, 7H), 7.24 (d, J=16.6 Hz, 1H), 7.18-7.11 (m, 1H), 6.95 (d, J=8.9 Hz, 1H), 5.16 (s, 2H).

Provenance & Evidence