(alphaS)-2,5-Difluoro-alpha-methylbenzenemethanol → 5-Bromo-3-[(R)-1-(2,5-difluoro-phenyl)ethoxy]-2-nitro-pyridine

HRID 1406272Notes

Reaction equation

HRID 1406272 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([OH:11])[C:5]([N+:8]([O-:10])=[O:9])=[N:6][CH:7]=1.[F:12][C:13]1[CH:18]=[CH:17][C:16]([F:19])=[CH:15][C:14]=1[C@@H:20](O)[CH3:21]>>[Br:1][C:2]1[CH:3]=[C:4]([O:11][C@@H:20]([C:14]2[CH:15]=[C:16]([F:19])[CH:17]=[CH:18][C:13]=2[F:12])[CH3:21])[C:5]([N+:8]([O-:10])=[O:9])=[N:6][CH:7]=1

Participants

3

Reactant 2

HCID 25324424(alphaS)-2,5-Difluoro-alpha-methylbenzenemethanolHCID 534184205-Bromo-2-nitropyridin-3-ol

Product 1

HCID 674677245-Bromo-3-[(R)-1-(2,5-difluoro-phenyl)ethoxy]-2-nitro-pyridine

Procedure

The title compound was prepared by a similar method to that of preparation 18 using commercially available 5-bromo-3-hydroxy-2-nitro-pyridine and (S)-1-(2,5-difluoro-phenyl)-ethanol except the reaction time was 1 hr and crude reaction purified by chromatography on silica gel eluting with ethyl acetate in heptane (50:50) to give a yellow oil (21.0 g, 93%).

Workup

  1. customcrude reaction
  2. custompurified by chromatography on silica gel eluting with ethyl acetate in heptane (50:50)

Sources & evidence

ORD record
ord-c9ecff418d9047bf955e07a52be0266d
Source dataset
uspto-grants-2014_12
Patent number
US08916593B2

Reaction notes

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