(4-Dodecylphenyl)boronic acid

121-43-7

126930-72-1

7732-18-5

206763-93-1

1. In a dry reaction flask, magnesium shavings (3.3 g) and tetrahydrofuran (20 ml) were added and placed in air. 2. A solution of 1-bromo-4-dodecylbenzene (40.1 g) in tetrahydrofuran (100 ml) was added slowly and dropwise at a rate that maintained reflux to prepare (4-dodecylphenyl)magnesium bromide Grignard reagent. 3. the reaction mixture was cooled to 0°C in an ice-water bath. 4. Slowly add trimethyl borate (15.4 g) dropwise, controlling the rate of dropwise acceleration to maintain the reaction temperature. 5. after completion of the dropwise addition, remove the ice water bath, allow the reaction mixture to come to room temperature and continue stirring for 1 hour. 6. Water (electrophoretic grade) was slowly added to the reaction mixture followed by concentrated hydrochloric acid (16 ml) and stirring was continued for 30 minutes. 7. The reaction mixture was extracted with ethyl acetate and the organic layer was separated. 8. The organic layer was washed with water until neutral and then dried with anhydrous sodium sulfate. 9. The desiccant was removed by filtration and the filtrate was concentrated under reduced pressure to give white solid (4-dodecylphenyl)boronic acid (32 g).