Tetrahydrofuran → 4-Methyl-1-naphthaleneboronic acid

Temperature

-70 °C

To a 125 mL round-bottomed flask equipped with N2 inlet were added 1.78 g (11.4 mmol) 1-bromo-4-methylnaphthalene and 20 mL dry tetrahydrofuran. The solution was cooled to −70° C., and 5.49 mL (13.7 mmol) of a 2.5M solution of n-butyl lithium in hexane was added over 5 minutes, and the reaction stirred at −70° C. for 10 minutes. The solution was then treated with 2.34 mL (13.7 mmol) triethyl borate, stirred 5 minutes at −70° C., then warmed to room temperature and stirred 40 hours. The reaction was quenched with aqueous ammonium chloride solution, poured into 0.5 N hydrochloric acid, and extracted into ethyl acetate. The organic layer was washed with brine, dried over sodium sulfate, and evaporated to a white solid after trituration with hexane, mp 224-228° C., 1.9 g (90%).

1. customTo a 125 mL round-bottomed flask equipped with N2 inlet
2. stirringstirred 5 minutes at −70° C.
3. temperaturewarmed to room temperature
4. stirringstirred 40 hours
5. customThe reaction was quenched with aqueous ammonium chloride solution
6. additionpoured into 0.5 N hydrochloric acid
7. extractionextracted into ethyl acetate
8. washThe organic layer was washed with brine
9. dry with materialdried over sodium sulfate
10. customevaporated to a white solid after trituration with hexane, mp 224-228° C., 1.9 g (90%)

ORD record

ord-0cf355cc42b24d9782386e696377eb12

Source dataset

uspto-grants-2006_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07012078B2