Triisopropyl borate → 3,3-bis(fluoromethyl)-6-methylbenzo[c][1,2]oxaborol-1(3H)-ol

To a solution of 2-bromo-1-(1,3-difluoro-2-(methoxymethoxy)propan-2-yl)-4-methylbenzene (1.2 g, 3.9 mmol) in THF (20 mL) at −78° C. was added n-BuLi (4 mL, 9.75 mmol) dropwise. The mixture was stirred at −78° C. for additional 1 h and then triisopropyl borate (1.5 g, 7.9 mmol) in 10 mL of THF was added below −70° C. The resulting mixture was kept stirring at −78° C. for 30 min and allowed to warm to rt and stirred overnight. Then it was quenched with aqueous NH4Cl and extracted with EA. The organic layer was dried over Na2SO4 and concentrated under reduced pressure. The residue was purified on column chromatography to provide the product (0.5 g, yield 60%).

1. stirringThe resulting mixture was kept stirring at −78° C. for 30 min
2. temperatureto warm to rt
3. stirringstirred overnight
4. customThen it was quenched with aqueous NH4Cl
5. extractionextracted with EA
6. dry with materialThe organic layer was dried over Na2SO4
7. concentrationconcentrated under reduced pressure
8. customThe residue was purified on column chromatography

ORD 기록

ord-b1ff79f610cb4007879e2b3ab5fb9230

출처 데이터셋

uspto-grants-2013_10

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US08546357B2