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

Temperature

-78 °C

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 record

ord-2c189c0f185648249dbc03c20f9c60ad

Source dataset

uspto-grants-2013_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08546357B2