(Diethylamino)sulfur trifluoride → 2-Bromo-6-(fluoromethyl)pyridine

Temperature

-78 °C

A solution of (6-bromopyridin-2-yl)methanol (5 g, 27 mmol) in dry DCM (60 mL) was added dropwise at −78° C. to a cooled solution of DAST (13 g, 80 mmol) in dry DCM (50 mL). The reaction mixture was stirred 1 h at −78° C. then 1 h at room temperature. To complete the reaction, an additional 5 mL of DAST were slowly added at −60° C. and the reaction mixture was kept overnight at room temperature. The reaction was quenched with water and the organic layer extracted with DCM, dried over MgSO4 and evaporated. Purification over silicagel chromatography (prepacked 85 g silicagel column, Cyclohexane/AcOEt:90/10 as eluent) to afford 4.50 g of 2-bromo-6-(fluoromethyl)pyridine (Yield: 89%) as pale yellow oil which crystallized at 0° C.

1. custom1 h
2. customat room temperature
3. customthe reaction
4. waitthe reaction mixture was kept overnight at room temperature
5. customThe reaction was quenched with water
6. extractionthe organic layer extracted with DCM
7. dry with materialdried over MgSO4
8. customevaporated
9. customPurification over silicagel chromatography (prepacked 85 g silicagel column, Cyclohexane/AcOEt:90/10 as eluent)

ORD record

ord-bc068a64ed4c4f77a37206ca5bdd9866

Source dataset

uspto-grants-2014_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08674106B2