Cornforth reagent → (5-Chloro-2-nitro-phenyl)-(6-chloro-pyridin-3-yl)-methanone

HRID 29501

Reaction equation

HRID 29501 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N+:17]([O-:19])=[O:18])=[C:6]([CH:8]([C:10]2[CH:11]=[N:12][C:13]([Cl:16])=[CH:14][CH:15]=2)[OH:9])[CH:7]=1.C1C=C[NH+]=CC=1.C1C=C[NH+]=CC=1.[O-][Cr](O[Cr]([O-])(=O)=O)(=O)=O>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N+:17]([O-:19])=[O:18])=[C:6]([C:8]([C:10]2[CH:11]=[N:12][C:13]([Cl:16])=[CH:14][CH:15]=2)=[O:9])[CH:7]=1

Participants

4

Reactant 2

HCID 2724130Cornforth reagent2×HCID 22327314(5-Chloro-2-nitro-phenyl)-(6-chloro-pyridin-3-yl)-methanol

Product 1

HCID 22327306(5-Chloro-2-nitro-phenyl)-(6-chloro-pyridin-3-yl)-methanone

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To (5-Chloro-2-nitro-phenyl)-(6-chloro-pyridin-3-yl)-methanol was added an excess (ca. 2 eq.) of PDC in DCM. The suspension was shaken at room temperature overnight. The reaction was monitored by LC-MS, another 1-2 eq. of PDC was added and the reaction was shaken for another 6 hours. The crude product was filtered through Celite and purified by flash chromatography (silica gel, DCM). 1H NMR (CDCl3): δ (ppm): 7.50 (d, J=2.4 Hz, 1H), 7.79 (d, J=8.0 Hz, 1H), 7.68 & 7.70 (dd, J=8.8 Hz, 2.0 Hz, 1H), 8.09-8.11 (m, 1 H), 8.24 (d, J=8.8 Hz, 1 H), 8.57 (d, J=2.0 Hz, 1 H. MS: (M+H)/z=296.9

Workup

  1. stirringthe reaction was shaken for another 6 hours
  2. filtrationThe crude product was filtered through Celite
  3. custompurified by flash chromatography (silica gel, DCM)

Sources & evidence

ORD record
ord-65646e9902364857ae21534a90002e81
Source dataset
uspto-grants-2008_09
Patent number
US07420055B2

Linked notes

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