HCID 86602988, compound → HCID 86672833, compound

HRID 1423035Notes

Reaction equation

HRID 1423035 reaction equation
[Br:1][C:2]1[N:7]=[C:6]([CH:8]([C:10]2[CH:15]=[CH:14][C:13]([F:16])=[CH:12][CH:11]=2)[OH:9])[CH:5]=[CH:4][CH:3]=1.[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1>ClCCl>[Br:1][C:2]1[N:7]=[C:6]([C:8]([C:10]2[CH:15]=[CH:14][C:13]([F:16])=[CH:12][CH:11]=2)=[O:9])[CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 86602988HCID 86602988, compoundHCID 178418287HCID 178418287, compound

Product 1

HCID 86672833HCID 86672833, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a chilled (0° C.) solution of (6-bromopyridin-2-yl)-(4-fluorophenyl)-methanol (6.2 g, 22 mmol) in dichloromethane (88 mL) is added pyridinium chlorochromate (PCC) (7.1 g, 33 mmol). The reaction mixture is allowed to warm to room temperature. After 5 hours, the reaction mixture is concentrated and purified by silica gel chromatography eluting with 10% EtOAc in hexanes to afford (6-bromopyridin-2-yl)-(4-fluorophenyl)-methanone.

Workup

  1. concentrationthe reaction mixture is concentrated
  2. custompurified by silica gel chromatography
  3. washeluting with 10% EtOAc in hexanes

Sources & evidence

ORD record
ord-e5e32ee519cf4ff8bbabe7840f1fe87f
Source dataset
uspto-grants-2015_01
Patent number
US08927550B2

Reaction notes

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