Diethyl Ether → 5-Bromo-2-ethylpyridine

A solution of ethylmagnesium bromide in dry ether (3M; 100 ml, 0.30 mol) was added dropwise to a stirred, ice-cooled solution of anhydrous zinc chloride (40.9 g, 0.30 mol) in dry tetrahydrofuran (500 ml) under nitrogen and the resulting solution stirred for a further 1 hour before the sequential addition of tetrakis (triphenylphosphine)palladium(0) (1.0 g, 0.87 mmol) and a solution of 2,5-dibromopyridine (50 g, 0.21 mol) in dry tetrahydrofuran (200 ml). The resulting yellow suspension was stirred at room temperature for 18 hours, quenched by the addition of water (200 ml) and evaporated under reduced pressure. The residue was partitioned between dichloromethane (500 ml) and a suspension of ethylenediaminetetraacetic acid (200 g) in water (1 l). The organic phase was separated, combined with a dichloromethane extract (500 ml) of the aqueous phase, dried (MgSO4) and evaporated under reduced pressure. Distillation under reduced pressure of the residue gave the title compound (28.8 g) as a colourless oil, b.p. 123-124° C./8 kPa (60 mm Hg). δ(CDCl3): 1.30(3H,t), 2.80(2H,q), 7.10(1H,d), 7.70(1H,dd), 8.60(1H,d).

1. customquenched by the addition of water (200 ml)
2. customevaporated under reduced pressure
3. customThe residue was partitioned between dichloromethane (500 ml)
4. additiona suspension of ethylenediaminetetraacetic acid (200 g) in water (1 l)
5. customThe organic phase was separated
6. extractionextract (500 ml) of the aqueous phase
7. dry with materialdried (MgSO4)
8. customevaporated under reduced pressure
9. distillationDistillation under reduced pressure of the residue

ORD record

ord-034ed8a99ced4b80a3146b9292101571

Source dataset

uspto-grants-1999_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05981560