Water → 5-Chloro-3-[(2,6-difluorobenzyl)oxy]-2-nitropyridine

HRID 2401629Notes

Reaction equation

HRID 2401629 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([OH:11])[C:5]([N+:8]([O-:10])=[O:9])=[N:6][CH:7]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[F:18][C:19]1[CH:26]=[CH:25][CH:24]=[C:23]([F:27])[C:20]=1[CH2:21]Br.O>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([O:11][CH2:21][C:20]2[C:19]([F:18])=[CH:26][CH:25]=[CH:24][C:23]=2[F:27])[C:5]([N+:8]([O-:10])=[O:9])=[N:6][CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 10796Cesium carbonateHCID 5814352-(Bromomethyl)-1,3-difluorobenzeneHCID 187656985-Chloro-2-nitropyridin-3-ol

Product 1

HCID 867178765-Chloro-3-[(2,6-difluorobenzyl)oxy]-2-nitropyridine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

33 g of 5-chloro-2-nitropyridin-3-ol (Example 12A; 189 mmol, 1 equivalent) and 61.6 g of caesium carbonate (189 mmol, 1 equivalent) were initially charged in 528 ml of DMF, 40.4 g of 2,6-difluorobenzyl bromide (189 mmol, 1 equivalent) were added and the mixture was stirred at RT overnight. The reaction mixture was stirred into a water/1N aqueous hydrochloric acid mixture. The solid obtained was filtered off, washed with water and air-dried. This gave 54.9 g (97% of theory) of the title compound.

Workup

  1. customThe solid obtained
  2. filtrationwas filtered off
  3. washwashed with water
  4. customair-dried

Sources & evidence

ORD record
ord-71f0018615a440b8a085dbc06266485f
Source dataset
uspto-grants-2014_08
Patent number
US08796305B2

Reaction notes

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