Piconol → 2-((2-Chloro-4-nitrophenoxy)methyl)pyridine

HRID 415013Notes

Reaction equation

HRID 415013 reaction equation
[H-].[Na+].[N:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH2:9][OH:10].[Cl:11][C:12]1[CH:17]=[C:16]([N+:18]([O-:20])=[O:19])[CH:15]=[CH:14][C:13]=1F>CN(C=O)C>[Cl:11][C:12]1[CH:17]=[C:16]([N+:18]([O-:20])=[O:19])[CH:15]=[CH:14][C:13]=1[O:10][CH2:9][C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][N:3]=1

Participants

5

Reactant 3

HCID 11474PiconolHCID 24758Sodium hydrideHCID 676882-Chloro-1-fluoro-4-nitrobenzene

Product 1

HCID 174694332-((2-Chloro-4-nitrophenoxy)methyl)pyridineYield 100%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

Sodium hydride (95%, 0.935 g, 37 mmol) is suspended in dry DMF (20 ml) under a nitrogen atmosphere and the resulting mixture is cooled in ice water. To above suspension is added dropwise over 15 minutes pyridin-2-yl-methanol (3.42 g, 31.3 mmol) in dry DMF (20 mL). Next, to the cold reaction mixture is added dropwise over 20 minutes a solution of 2-Chloro-1-fluoro-4-nitro-benzene (5 g, 28.5 mmol) in dry DMF (20 ml). Upon the end of addition the cold bath is removed and the reaction mixture is stirred for another 36 hours. Water (80 mL) was added slowly to the reaction mixture, and a yellow precipitate resulted. The resultant solid is isolated by suction filtration, washed with water (80 ml), and air dried to yield 7.52 g (28.5 mmol, 100%) of the clean desired material as a yellow powder.

Workup

  1. customNext, to the cold reaction mixture
  2. additionUpon the end of addition the cold bath
  3. customis removed
  4. additionWater (80 mL) was added slowly to the reaction mixture
  5. customa yellow precipitate resulted
  6. customThe resultant solid is isolated by suction filtration
  7. washwashed with water (80 ml), and air
  8. customdried

Sources & evidence

ORD record
ord-22b5019fc7fb4e2082fe4c475f060d73
Source dataset
uspto-grants-2012_01
Patent number
US08088766B2

Reaction notes

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