Hydrochloric Acid → (6-Phenyldibenzo[b,d]thiophen-4-yl)boronic acid

Participants

Reaction Conditions

Reaction Steps

3.5 g (13.4 mmol) 4-phenyldibenzothiophene was dissolved in ˜30 mL anhydrous THF in a three necked 250 mL flask and cooled down to −78° C. To the mixture, 17 mL (27 mmol) 1.6 M BuLi in hexane was added and stirred for 30 minutes. The cooling batch was removed and let reaction kept stirring for overnight. The reaction mixture was cooled down again to −78° C. and 4.5 mL (40 mmol) trimethyl borate was added and stirred at room temperature for 4 hours. ˜100 1M HCl was added and kept stirring for 1 hour. The mixture was extracted by ethyl acetate and the organic extracts were combined. The solvent was evaporated to dryness. The solid was added with ˜100 mL 20% ethyl acetate in hexane was stirred for few hours and then filtered. The filtered solid washed by hexane few times. ˜2.5 g white solid was obtained as product which was confirmed by proton NMR.

Provenance & Evidence