Carbon Dioxide → HCID 58950766, compound

Participants

Reaction Steps

To a stirring solution of β-tetralone (34) (1.00 g, 6.84 mmol) and pd(dba)2 (39 mg, 1 mol%) in toluene was added t-Bu3P (228 uL, 10 wt % in hexanes, 1.1%). The solution was chilled (dry-ice bath) before adding LiHMDS (7.5 mL, 1M in hexanes, 1.1 eq) followed by 1-bromo-3,4-dichlorobenzene (1 mL, 1.1 eq). The solution was then allowed to warm to ambient temperature and heated under microwave radiation for 5 minutes (maximum temperature 140° C.). After cooling, the reaction was quenched with aqueous ammonium chloride and extracted with MTBE. The organic layer was dried with sodium sulfate, filtered through celite, and evaporated. The crude oil was separated on silic gel to give the title compound (1.45 g, 73%) as a slight brown oil. This material was assayed as 90% pure. TLC Rf (25% EA/Hex)=0.42. GCMS Rt=13.21 min m/z=290 (M+). 1H NMR (CDCl3, δ): 7.37 (d, J=8.3 Hz, 1H), 7.3-7.2 (m, 3H), 7.17 (d, J=2.1 Hz, 1H), 6.9 (m, 2H), 4.68 (s, 1H), 3.1 (m, 2H), 2.7 (m, 2H). 13C NMR (CDCl3, δ): 208.4, 137.7, 136.7, 135.3, 132.7, 131.5, 130.7, 130.5, 129.2, 128.2, 128.1, 127.7, 127.3, 58.6, 37.1, 28.0.

Provenance & Evidence