Trimethyl borate → (2,4-Difluoro-5-methylphenyl)boronic acid

To 94A (2.8 g, 11 mmol) in THF (50 mL) was added n-BuLi (1.6M in hexane, 8.9 mL) at −78° C. After 10 min stirring, trimethyl borate (2.5 mL) was introduced. The mixture was stirred from −78° C. to rt overnight. The reaction was quenched by 1N HCl and extracted with EtOAc. The organic layer was separated and washed with saturated Na2S2O3, brine and dried over MgSO4. Evaporation of solvent gave product 94B (1.66 g, 88% yield) as a white solid. 1H NMR (400 MHz, CDCl3) δ ppm 2.22 (s, 3H) 6.82 (t, J=9.23 Hz, 1H) 7.26 (t, J=7.69 Hz, 1H).

1. stirringThe mixture was stirred from −78° C. to rt overnight
2. customThe reaction was quenched by 1N HCl
3. extractionextracted with EtOAc
4. customThe organic layer was separated
5. washwashed with saturated Na2S2O3, brine
6. dry with materialdried over MgSO4
7. customEvaporation of solvent

ORD 기록

ord-97be1919d98d44e1ad3466b7eac6b47c

출처 데이터셋

uspto-grants-2009_11

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US07622585B2