Ethylene Glycol → HCID 86665968, compound

Participants

Reaction Steps

A mixture of 2-naphthalenethiol (15.5 g, 0.097 mol), 9-bromoanthracene (25.0 g, 0.0.097 mol), CuI (19.1 g, 0.1 mol), K2CO3 (15.0 g, 0.11 mol), KI (16.6 g, 0.1 mol) and ethylene glycol (10 mL) in tert-amyl alcohol (500 mL) were refluxed for 48 h under N2. After cooling, dichloromethane was added and the mixture washed with 2N NaOH and water, and filtered through an alumina plug. Solvent was removed by rotary evaporation under vacuum and the residue purified by column chromatography (silica/hexanes) to yield 16.5 g (50.5%) of the sulfide. 1H NMR (CDCl3) δ 7.13 (dd, J=8.7, 1.85 Hz, 1H) 7.28-7.35 (m, 3H), 7.43-7.47 (m, 1H), 7.49-7.56 (m, 4H), 7.58 (d, J=8.7 Hz, 1H), 7.66-7.70 (m, 1H), 8.06-8.10 (m, 2H), 8.64 (s, 1H), 8.84-8.89 (m, 2H).

Provenance & Evidence