[2-(bromomethyl)phenyl]boronic acid

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution in DMF (2.0 ml) of [2-(bromomethyl)phenyl]boronic acid (399 mg) was added in one portion to a stirred slurry of sodium methanesulphinate (200 mg) in DMF (2.0 ml). The mixture was stirred for 2.5 h i nd then poured into 1M hydrochloric acid (100 ml) and extracted with EA (3×50 ml). the combined extracts were dried and evaporated. On standing a solid material precipitated, which was washed with ER to give white crystals of the title compound (115 mg), m.p. 133°-137°. T.l.c. (A) ER:hexane (3:2) Rf 0.51. extracted with EA (3×50 ml) the combined extracts were dried evaporated precipitated which was washed with ER

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution in DMF (2.0 ml) of [2-(bromomethyl)phenyl]boronic acid (399 mg) was added in one portion to a stirred slurry of sodium methanesulphinate (200 mg) in DMF (2.0 ml). The mixture was stirred for 2.5 h i nd then poured into 1M hydrochloric acid (100 ml) and extracted with EA (3×50 ml). the combined extracts were dried and evaporated. On standing a solid material precipitated, which was washed with ER to give white crystals of the title compound (115 mg), m.p. 133°-137°. T.l.c. (A) ER:hexane (3:2) Rf 0.51. extracted with EA (3×50 ml) the combined extracts were dried evaporated precipitated which was washed with ER

Conditions: temp:82.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A suspension of 2-methylphenylboronic acid (10.65 g), N-bromosuccinimide (NBS, 16.86 g) and 2,2′-azobisisobutyronitrile (AIBN, 1.708 g) in carbon tetrachloride (1000 mL) was heated in an oil bath at 82° C. to reflux for 2 hours under anhydrous condition. Cooled the reaction mixture to room temperature and filtered off the solid. Extracted the filtrate with water (2×200 mL). The organic layer was separated, dried over MgSO4 and concentrated in vacuo to dryness. Redissolved the solid in methanol (100 mL) and added ethyl acetate (1000 mL) to it. The resultant precipitate was collected, washed with ethyl acetate (2×50 mL) and dried in the air. The filtrate was concentrated to a small volume and a second crop of solid was also collected. The combined solid was dried in an oven under high vacuum at 50° C. overnight. There was obtained 6.48 g (39%) of product. to reflux for 2 hours under anhydrous condition Cooled the reaction mixture to room temperature filtered off the solid Extracted the filtrate with water (2×200 mL) The organic layer was separated dried over MgSO4 concentrated in vacuo to dryness Redissolved the solid in methanol (100 mL) added ethyl acetate (1000 mL) to it The resultant precipitate was collected washed with ethyl acetate (2×50 mL) dried in the air The filtrate was concentrated to a small volume a second crop of solid was also collected The combined solid was dried in an oven under high vacuum at 50° C. overnight