Hexane → 2-Acetyl-6-bromopyridine

Temperature

-80 °C

To a solution of 2,6-dibromopyridine (0.75 mol) in 2000 ml of anhydrous ether, which was cooled to −60° C. under N2, was added a solution of n-butyllithium in hexane (0.75 mol) over 15 min. The reaction mixture was cooled to −80° C. and a solution of dimethylacetamide (0.86 mol) in 70 ml anhydrous ether was added slowly over 1 hour. After stirring the mixture for 15 min, a solution of NH4Cl (0.93 mol) in 150 ml of water was added slowly over 8 min. After stirring an additional 45 min at room temperature, the aqueous layer was separated and extracted with 500 ml of ether. The combined organic layer was washed with water (2×800 ml), dried (MgSO4), filtered, and stripped on a rotary evaporator to yield 159 g of the desired product. This material was distilled at 80° C./0.1 mm Hg to give a near colorless oil that crystallized readily on cooling.

1. stirringAfter stirring an additional 45 min at room temperature
2. customthe aqueous layer was separated
3. extractionextracted with 500 ml of ether
4. washThe combined organic layer was washed with water (2×800 ml)
5. dry with materialdried (MgSO4)
6. filtrationfiltered
7. customstripped on a rotary evaporator

ORD record

ord-7e24365779ab4a1d96daa26ee98a970a

Source dataset

uspto-grants-2001_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06248870B1