Pyridinium → HCID 59459870, compound

HRID 1503799Notes

Reaction equation

HRID 1503799 reaction equation
[NH+]1C=CC=CC=1.C1C=C[NH+]=CC=1.[O-][Cr](Cl)(=O)=O.[Br:18][C:19]1[CH:20]=[C:21]([CH2:27][OH:28])[CH:22]=[C:23]([Br:26])[C:24]=1[Cl:25]>C(Cl)(Cl)Cl>[Br:18][C:19]1[CH:20]=[C:21]([CH:22]=[C:23]([Br:26])[C:24]=1[Cl:25])[CH:27]=[O:28]

Participants

5

Reactant 3

HCID 4989215PyridiniumHCID 86722584HCID 86722584, compoundHCID 178418287HCID 178418287, compound

Product 1

HCID 59459870HCID 59459870, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Pyridinium chlorochormate (PCC, 3.44 g, 15.9 mmol) was added in one portion to a stirred solution of (3,5-dibromo-4-chlorophenyl)methanol (3.2 g, 11.0 mmol) in CHCl3 (40 mL) at ambient temperature and the reaction mixture was stirred overnight. The reaction mixture was filtered through Celite®, the Celite® pad was washed with CHCl3 and the filtrate was concentrated to afford the title compound as an off white solid (2.0 g, 62%): mp 110-113° C.; 1H NMR (300 MHz, DMSO-d6) δ 9.93 (s, 1H), 8.27 (s, 2H); ESIMS m/z 297.0 ([M]+).

Workup

  1. filtrationThe reaction mixture was filtered through Celite®
  2. washthe Celite® pad was washed with CHCl3
  3. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-f5d4f3972d1b4a41a5e17f1c3ade35cc
Source dataset
uspto-grants-2015_12
Patent number
US09212164B2

Reaction notes

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