Dimethylformamide → 4-(1,1,1,3,3,3-Hexafluoro-2-hydroxypropan-2-yl)-2-propylbenzaldehyde

Temperature

-78 °C

To a nitrogen purged 3-necked flask was added 2-(4-bromo-3-propylphenyl)-1,1,1,3,3,3-hexafluoropropan-2-ol (2.74 mmol, 1 g) in anhydrous tetrahydrofuran (15 mL). The solution was cooled to −78° C. before the addition of n-butyl lithium in hexane (2.5M, 8.22 mmol, 3.29 mL). The mixture was stirred at −78° C. for 15 minutes before the drop wise addition of N,N-dimethylformamide (3.01 mmol, 0.220 g). The mixture was stirred at −78° C. for 10 minutes and was then allowed to warm to room temperature and stir for 30 minutes. The mixture was quenched with water (10 mL) and diluted with ethyl acetate (100 mL). The organic phase was separated, washed with water (2×50 mL), dried over magnesium sulfate, filtered and the filtrate was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (eluting with 10% ethyl acetate/90% heptane) to afford the title compound (417 mg). MS (ESI) m/z 313.3 [M−H]−

1. temperatureto warm to room temperature
2. stirringstir for 30 minutes
3. customThe mixture was quenched with water (10 mL)
4. additiondiluted with ethyl acetate (100 mL)
5. customThe organic phase was separated
6. washwashed with water (2×50 mL)
7. dry with materialdried over magnesium sulfate
8. filtrationfiltered
9. concentrationthe filtrate was concentrated under reduced pressure
10. customThe resulting residue was purified by silica gel column chromatography (eluting with 10% ethyl acetate/90% heptane)

ORD record

ord-409a9fdb504e49ff8b9b4ea39c629720

Source dataset

uspto-grants-2015_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09108939B2