Benzaldehyde → (5-bromopyridin-2-yl)(phenyl)methanol

Temperature

-70 °C

2,5 dibromopyridine (15.0 g, 63.3 mmol) was added to toluene (450 ml) and it was cooled at −70° C. BuLi (1.6 M in hexanes)(41 ml, 66.5 mmol, 1.05 eg) was added dropwise over 1 hour, then reaction mixture was stirred at −70° C. for another hour. Benzaldehyde (7.4 g, 69.6 mmol, 1.1 eg) dissolved in toluene (5 mL) was added slowly. The mixture was stirred at −70° C. for 30 min., then warmed to 0° C. Quenched with Sat NH4Cl (200 mL) and phases partitioned. Aqueous phase was extracted with EtOAc (100 mL) and combined organic washed with brine, dried, evaporated. Residue was chromatographed with 15% EtOAc/hexane to yield the title compound.

1. customreaction mixture
2. additionwas added slowly
3. stirringThe mixture was stirred at −70° C. for 30 min.
4. temperaturewarmed to 0° C
5. customQuenched with Sat NH4Cl (200 mL) and phases
6. custompartitioned
7. extractionAqueous phase was extracted with EtOAc (100 mL)
8. washcombined organic washed with brine
9. customdried
10. customevaporated
11. customResidue was chromatographed with 15% EtOAc/hexane

ORD record

ord-c6316ac4d11b4c218f6cb04584151146

Source dataset

uspto-grants-2007_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07279478B2