Acetic acid, 2-(triphenylphosphoranylidene)-, ethyl ester → Ethyl 3-(5-Bromo-2-pyridyl)acrylate

5-Bromopyridine-2-carbaldehyde (502 mg, 2.70 mmol) was added to a solution of ethyl (triphenyl-λ5-phosphanylidene)acetate (1570 mg, 4.51 mmol) in DMF (5.00 mL) and the reaction mixture was stirred at room temperature for 40 minutes. The mixture was poured into ice-water, and extracted with ethyl acetate. The organic layer was washed with brine, dried and concentrated under reduced pressure. A mixture of hexane:ethyl acetate (2:1) was added to the crude residue and the insoluble materials were filtered off. The filtrate was concentrated under reduced pressure and purified by silica gel chromatography (4% ethyl acetate in hexanes) to afford ethyl-3-(5-bromopyridin-2-yl)prop-2-enoate MS APCI calc'd for C10H11BrNO2 [M+H]+ 256 and 258. found 256 and 258.

1. extractionextracted with ethyl acetate
2. washThe organic layer was washed with brine
3. customdried
4. concentrationconcentrated under reduced pressure
5. additionA mixture of hexane:ethyl acetate (2:1)
6. additionwas added to the crude residue
7. filtrationthe insoluble materials were filtered off
8. concentrationThe filtrate was concentrated under reduced pressure
9. custompurified by silica gel chromatography (4% ethyl acetate in hexanes)

ORD record

ord-1145c1b86c984c43b2df25d77a3d3d21

Source dataset

uspto-grants-2016_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09376418B2