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A 500-mL, four-necked, round-bottomed flask containing magnesium turnings () is equipped with a mechanical stir, a thermometer, a press-equalizing dropping funnel, a reflux condenser fitted with an nitrogen inlet adapter. The system is dried and flushed with nitrogen. Anhydrous THF () is introduced to cover the magnesium, a crystal of iodine is added. The dropping funnel is filled with a solution fo bromobenzene () in 100-mL THF. Approximately 10 ml of the solution is added to the flask, and the contents are stirred until the Grignard reaction commences. The remainder of the aryl bromide solution is added slowly at a rate such that the mixture reflux(addition time ca. 1 hour). The resulting mixture is stirred refluxing for another 1 hour.
The mixture is cooled to approximately -50 ¡æ while stirring. A solution of g trimethyl borate in 100 ml THF is added dropwise at a rate such that the mixture temperature maintain -50~-40 ¡æ (addition time ca. 1 hour). Following the addition, the mixture was allowed to stir at -50~-40 ¡æ for another 1 hour.
The resulting mixture is heated slowly to -15 ¡æ while stirring. A solution of 10% hydrochloride acid is added to the reactor. After stirring 1 hour, the organic layer is separated and the aqueous layer is extracted with three 100-mL of ethyl acetate. The combined organic layers are washed with water (100mL), and concentrated under reduced pressure to remove most of solvent. The resulting white solid is dissolved in a minimal amount of hot (65¡ãC) ethyl acetate ,
allowed to cool to room temperature, and then 600 mL of hexane is added. The resulting solution is
allowed to stand overnight and then filtered to afford pure boronic acid as white
crystals.solid
3Â¥2007-11-27 10:52:35
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whh8308(½ð±Ò+1,VIP+0):duoxie 3-25 12:55
also see:Organic Syntheses, Coll. Vol. 10, p.80 (2004); Vol. 79, p.176 (2002).
4Â¥2007-11-27 10:55:11
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