2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane → 3-[3,5-Difluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenoxy]tetrahydro-2H-pyran

To a mixture of 3-(3,5-difluorophenoxy)tetrahydro-2H-pyran (1.42 g, 6.63 mmol) in THF (26 mL) at −78° C., a solution of n-BuLi in hexanes (1.6 M; 10.4 mL, 16.6 mmol) was added slowly through a dripping funnel. When addition was complete, the mixture was kept at −78° C. for 1 h. 2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (4.06 mL, 19.9 mmol) was then added in one portion. The mixture was allowed to warm to room temperature and stirred for 1 h. The mixture was quenched with NaHCO3 solution and extracted with EtOAc. The organic extract was washed with brine, dried over Na2SO4, and concentrated under reduced pressure to give sub-title compound as a colorless oil. LCMS calc. for C17H24BF2O4 (M+H)+ m/z=341.2. found: 341.1.

1. additionWhen addition
2. customThe mixture was quenched with NaHCO3 solution
3. extractionextracted with EtOAc
4. extractionThe organic extract
5. washwas washed with brine
6. dry with materialdried over Na2SO4
7. concentrationconcentrated under reduced pressure

ORD record

ord-8b43a5378ca34d4eb56e6c43ece6ad08

Source dataset

uspto-grants-2015_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09200004B2