Bromine → HCID 68537594, compound

Participants

Reaction Steps

To a solution of 6-Methoxy-3-propyl-3,4-dihydro-2H-naphthalen-1-one (93) (1.6 g, 7.33 mmol) in dry chloroform (65 mL) was added dropwise via an addition funnel bromine (2.35 g, 14.7 mmol) in chloroform (20 mL). The reaction mixture was stirred at ambient temperature for 20 h. The reaction mixture was concentrated to afford the title compound as oil, 2.76 g. The crude material (2.76 g, 7.33 mmol) in dry acetonitrile (64 mL) was cooled to −10° C., 1,8-diazabicyclo[5.4.0]undec-7-ene (1.64 mL, 10.99 mmol) in dry acetonitrile (8 mL) was added dropwise via an addition funnel. The reaction mixture was quenched with 1 N HCl (50 mL) after stirring for 1 h at 6° C. The aqueous layer was extracted with EtOAc, the organic layer was washed with brine, dried over MgSO4, filtered and concentrated. The crude product was purified with 1:9 EtOAc:hexanes over 40 min to obtain 1.41 g (65%) of the title compound (94). 1H NMR (400 MHz, d-CDCl3): δ 1.01 (t, J=7.3 Hz, 3H), 1.68-1.74 (m, 2H), 2.79 (t, J=7.7 Hz, 2H), 3.90 (s, 3H), 6.06 (s, 1H), 7.00-7.01 (m, 1H), 7.08 (dd, J1=2.6 Hz, J2=9.1 Hz, 1H), 7.17 (s, 1H), 8.07 (d, J=9.1 Hz, 1H).

Provenance & Evidence