Propargyl alcohol → [4-(3-hydroxy-1-propynyl)phenyl]boronic Acid

Participants

Reaction Conditions

Reaction Steps

Pyrrolidine (100 mL) was added to a mixture of 4-iodophenylboronic acid (19.83 g, 80.01 mol) and Pd(Ph3P)4 (0.93 g, 0.80 mmol) and the mixture was stirred for 5 min to give a solution. The solution was cooled to 0° C. and propargyl alcohol (9.4 mL, 161.5 mol) was added. The resulting solution was stirred for 1 h at 0° C. and 18 h at room temperature and then concentrated in vacuo. The residue was diluted with 2 N NaOH (200 ml), washed with dichloromethane (2×100 mL), cooled to 0° C., and acidified with 10% HCl. The precipitated solids were isolated by filtration, washed with water and dried in vacuo to provided 12.76 g (91%) of the title compound as a tan solid. MS 175 (M−H)−.

Provenance & Evidence