Isopropanol → HCID 67363825, compound

Participants

Reaction Steps

To a solution of triphosgene (1.485 mmol, 0.441 g) in tetrahydrofuran (20 ml) was added drop wise a solution of 4-amino-3-methoxyphenylboronic acid, pinacol ester (4.01 mmol, 1 g) and N,N-diisopropylethylamine (5.02 mmol, 0.829 ml) in tetrahydrofuran (30 ml) at room temperature. The temperature was kept between 20 and 30° C. After 30 minutes a solution of 2-propanol (8.03 mmol, 0.614 ml) and N,N-diisopropylethylamine (5.02 mmol, 0.829 ml) in tetrahydrofuran (20 ml) was added drop wise to the reaction mixture keeping the temperature between the 20-30° C. The reaction mixture was heated till reflux. After two hours an additional 10 ml of 2-propanol was added and the reaction mixture stirred at reflux temperature for 3 days. The reaction mixture was poured in water (150 ml) and extracted with ethyl acetate (150 ml). The organic layer was washed with 10% sodium chloride solution (10 ml), dried (magnesium sulfate) and evaporated till dryness to yield isopropyl 2-methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenylcarbamate (1.18 g) as a dark brown oil

Provenance & Evidence