Hexane → (5-Ethyl-2-fluorophenyl)boronic acid

To 84B (550 mg, 2.3 mmol) in THF (10 mL) was added 1.6 M n-butyllithium in hexane (2.2 ml, 3.5 mmol) at −78° C. After stirring for 1 h, trimethylborate (0.52 mL, 4.6 mmol) was introduced at −78° C. The reaction mixture was warmed up to rt overnight. It was then quenched by 1.0 N HCl (10 mL) and extracted with EtOAc (3×30 mL). The combined organic layers were washed with brine, dried over MgSO4, and concentrated. The crude product was purified by column chromatography to give 255 mg white solid of 84C. 1H NMR (400 MHz, Methanol-d4) δ ppm 1.15-1.27 (m, 3H) 2.61 (q, J=7.76 Hz, 2H) 6.94 (t, J=8.57 Hz, 1H) 7.17-7.27 (m, 2H).

1. customIt was then quenched by 1.0 N HCl (10 mL)
2. extractionextracted with EtOAc (3×30 mL)
3. washThe combined organic layers were washed with brine
4. dry with materialdried over MgSO4
5. concentrationconcentrated
6. customThe crude product was purified by column chromatography

ORD record

ord-90a4d68a06c7417898892fd098cabecd

Source dataset

uspto-grants-2009_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07622585B2