Ethyl Acetate → 3-Chloro-4-(1,4-dioxaspiro[4.5]dec-7-en-8-yl)benzenamine

Participants

Reaction Conditions

Reaction Steps

A 2N aqueous solution of potassium carbonate (26.5 mL) and tetrakis(triphenylphosphine) palladium(0) (1.23 g, 1.06 mmol) were added sequentially, each in one portion, to a stirred solution of 8-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,4-dioxaspiro[4.5]dec-7-ene (Intermediate 78ii, 5.65 g, 21.2 mmol) and 4-bromo-3-chloro aniline (4.39 g, 21.2 mmol) in dimethoxyethane (80 mL) at room temperature under an argon atmosphere. The reaction mixture was then heated at 80° C. for 24 h under an argon atmosphere. The reaction mixture was cooled to room temperature and ethyl acetate was added and then the mixture was washed twice with H2O and then brine. The organic layer was dried (MgSO4) and concentrated in vacuo to leave an oil, which was purified by column chromatography, using a gradient of 20-50% ethyl acetate:isohexane as eluent, to give the title compound (3.5 g, 62%) as a solid; 1H NMR δ 1.7-1.8 (2H, m), 2.26-2.43 (4H, m), 3.91 (4H, s), 5.28 (2H, s), 5.4-5.47 (1H, m), 6.45 (1H, dd), 6.59 (1H, d), 6.86 (1H, d).

Provenance & Evidence