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

HRID 403655

Reaction equation

HRID 403655 reaction equation
[OH-].[K+].[N:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH2:9][OH:10].[Cl:11][C:12]1[CH:13]=[C:14]([N+:19]([O-:21])=[O:20])[CH:15]=[CH:16][C:17]=1F.O>C(#N)C>[Cl:11][C:12]1[CH:13]=[C:14]([N+:19]([O-:21])=[O:20])[CH:15]=[CH:16][C:17]=1[O:10][CH2:9][C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][N:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11474PiconolHCID 14797Potassium HydroxideHCID 676882-Chloro-1-fluoro-4-nitrobenzene

Product 1

HCID 174694332-((2-Chloro-4-nitrophenoxy)methyl)pyridineYield 69.6%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Conditions

Temperature
35 °C

Procedure

A mixture of potassium hydroxide (20.6 g, 0.15 mol, 0.52 equiv) and 2-pyridylcarbinol (31.08 g, 0.285 mol, 1.00 equiv) in acetonitrile (750 ml) was stirred at 35° C. for 30 minutes. A solution of the 3-chloro-4-fluoronitrobenzene (50 g, 0.29 mol, 1.00 equiv) in acetonitrile (250 ml) was added and the mixture was stirred at 40° C. for 14 hours and then cooled to room temperature. Water (1000 ml) was added and the precipitated solids were filtered and washed with water and dried to give product 52.5 g. MS (ESI) m/z: 265 (M+1).

Workup

  1. stirringthe mixture was stirred at 40° C. for 14 hours
  2. temperaturecooled to room temperature
  3. filtrationthe precipitated solids were filtered
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-d3f649813b384047864f8537d31e75db
Source dataset
uspto-grants-2014_06
Patent number
US08748453B2

Linked notes

Loading…