2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → 1-(2-(4-(2-Bromo-6-methoxynaphthalen-1-yloxy)phenoxy)ethyl)piperidine

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Reaction Conditions

Reaction Steps

To a round bottom flask, add 1-(2-(4-(2-bromo-6-methoxy-3,4-dihydronaphthalen-1-yloxy)phenoxy)ethyl)piperidine (6.7 g, 6.6 mmol) and acetonitrile (50 mL). Stir the mixture at 25° C. for 5 min. Add 2,3-dichloro-5,6-dicyanobenzoquinone (DDQ) (3.2 g, 14.1 mmol) slowly to the reaction mixture. Heat the mixture to 80° C. and stir at the temperature for 14 hours. Cool the reaction mixture to room temperature and quench with ice-water. Extract the mixture with ethyl acetate three times and discard the aqueous phase. Dry the combined organic layers (MgSO4), filter, and concentrate to dryness. Purify by flash chromatography to give 1-(2-(4-(2-bromo-6-methoxynaphthalen-1-yloxy)phenoxy)ethyl)piperidine as a brown solid (817 mg). 1HNMR (d-DMSO, 300 MHZ): 7.68 (3H, m), 7.43 (1H, s), 7.15 (1H, m), 6.97 (2H, d), 6.72 (2H, d), 4.26 (2H, s), 3.85 (3H, s), 3.48 (4H, m), 2.96 (2H, m), 1.70 (6H, m).

Provenance & Evidence