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

HRID 2275765Notes

Reaction equation

HRID 2275765 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 water/1N aqueous hydrochloric acid. The solid was filtered off, washed with water and air-dried. This gave 54.9 g (97% of theory) of the title compound.

Workup

  1. filtrationThe solid was filtered off
  2. washwashed with water
  3. customair-dried

Sources & evidence

ORD record
ord-ea5147d32c874c4d8c817acee154475e
Source dataset
uspto-grants-2015_09
Patent number
US09126998B2

Reaction notes

Loading…