Triethyl borate → HCID 43145275, compound

Temperature

-78 °C

To a solution of 1-bromo-2-(isopentyloxy)benzene (9.68 g, 40 mmol) in THF (160 mL) was added dropwise n-butyl lithium (1.6 M in hexanes, 1.05 eq., 26.3 mL) under nitrogen at −78° C. over 30 min. After further stirring for 1 hour at −78° C., triethylborate (5.86 mL, 51.3 mmol) was added. The cooling bath was removed and the reaction mixture was stirred overnight at rt. An aqueous solution of 2 N HCl (20 mL) was added and the reaction solution stirred for 30 min, at which point 50 mL of water was added. The reaction mixture was extracted with ether (5×80 mL), dried over anhydrous sodium sulfate, filtrated and concentrated to yield 2-(isopentyloxy)phenylboronic acid (6.30 g, 77% yield). 1H NMR (400 MHz, CDCl3): 7.83 (d, 1H), 7.43 (dd, 1H), 7.03 (t, 1H), 6.93 (d, 1H), 6.05 (s, 2H), 4.10 (t, 2H), 1.86-1.75 (m, 3H), 1.0 (s, 6H).

1. customThe cooling bath was removed
2. stirringthe reaction mixture was stirred overnight at rt
3. additionAn aqueous solution of 2 N HCl (20 mL) was added
4. stirringthe reaction solution stirred for 30 min, at which
5. additionwas added
6. extractionThe reaction mixture was extracted with ether (5×80 mL)
7. dry with materialdried over anhydrous sodium sulfate
8. filtrationfiltrated
9. concentrationconcentrated

ORD record

ord-e00b2e438344430ca8e40a043c88bccb

Source dataset

uspto-grants-2012_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08101625B2