3-Pyridinecarboxaldehyde → Pyridine, 3-(2,2-dibromoethenyl)-

Tetrabromomethane (24.82 g, 0.747 mole) and triphenylphosphine (39.17 g, 0.149 mole) were stirred together in dry methylene chloride (100 mL) for 5 min. at 0° C. under a nitrogen atmosphere. To this mixture was added dropwise pyridine 3-carboxaldehyde (4 g, 0.0373 mole). The solution was then stirred for 45 min. at ambient temperature. The reaction mixture was extracted with aqueous 6N hydrochloric acid (3×25 mL), the aqueous layer basified with solid sodium bicarbonate to pH 8-9 and extracted with chloroform (4×25 mL). The combined organic liquours were dried over anhydrous sodium sulfate, filtered and concentrated on a rotary evaporator to give a dark colored syrup. The crude product was chromatographed on silica gel (70-230 mesh) with chloroform:methanol (95:5) as eluant, to afford a light yellow solid (5.0 g, 70%) which rapidly turned dark on standing.

1. extractionThe reaction mixture was extracted with aqueous 6N hydrochloric acid (3×25 mL)
2. extractionextracted with chloroform (4×25 mL)
3. dry with materialThe combined organic liquours were dried over anhydrous sodium sulfate
4. filtrationfiltered
5. concentrationconcentrated on a rotary evaporator
6. customto give a dark colored syrup
7. customThe crude product was chromatographed on silica gel (70-230 mesh) with chloroform:methanol (95:5) as eluant

ORD record

ord-d7edba51f018489380d4a887b1e9b6d1

Source dataset

uspto-grants-1998_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05731314