Ammonium Chloride → HCID 178439836, compound

Participants

Reaction Conditions

Reaction Steps

To a solution 1,4-dibromonaphthalene (28.6 g, 0.1 mol) in dry THF (800 mL) at −78° C. was added t-butyllithium (59.0 mL, 1.7 M solution in pentane, 0.1 mol) over a period of 20 min. After 30 min stirring at −78° C., allylchlorodimethylsilane (13.5 g, 0.1 mol) in THF (25 mL) was added dropwise over a period of 30 min. The reaction mixture was stirred further for 1 h and warmed to room temperature. Concentrated NH4Cl (5 mL) was added to the solution, and the reaction mixture was concentrated. The resulting yellow oil was concentrated, extracted with ethyl acetate/water, and the organic layer was dried, concentrated. The crude product was Kugelrohr distilled to give a colorless oil (25.6 g, 84%); 1H NMR (300 MHz, CDCl3) δ 0.57 (s, 6 H), 2.07 (d, J=8.10 Hz, 2 H), 4.94-5.04 (2 H), 5.87 (ddt, J=16.80, 10.20, 8.10 Hz, 1 H), 7.56 (d, J=7.20 Hz, 1 H), 7.61-7.70 (2 H), 7.83 (d, J=7.20 Hz, 1 H), 8.19 (m, 1 H), 8.43 (m, 1 H); 13C NMR (75 MHz, CDCl3) −1.5 (2 C), 24.5, 114.3, 126.0, 126.9, 127.1, 128.6, 128.8, 129.7, 132.2, 134.2, 134.7.

Provenance & Evidence