Water → Pyridine, 5-bromo-2-(3,4-dichlorophenoxy)-

HRID 474193Notes

Reaction equation

HRID 474193 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([Br:8])=[CH:4][N:3]=1.C([O-])([O-])=O.[K+].[K+].[Cl:15][C:16]1[CH:17]=[C:18]([OH:23])[CH:19]=[CH:20][C:21]=1[Cl:22].O>CN(C=O)C>[Br:8][C:5]1[CH:6]=[CH:7][C:2]([O:23][C:18]2[CH:19]=[CH:20][C:21]([Cl:22])=[C:16]([Cl:15])[CH:17]=2)=[N:3][CH:4]=1

Participants

6

Reactant 4

HCID 962WaterHCID 72583,4-DichlorophenolHCID 11430Potassium CarbonateHCID 693532,5-Dibromopyridine

Product 1

HCID 514889Pyridine, 5-bromo-2-(3,4-dichlorophenoxy)-Yield 100%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of 2,5-dibromopyridine (2.412 g, 10.18 mmol) in DMF (50 mL) was added K2CO3 (5.22 g, 37.8 mmol) and 3,4-dichlorophenol (2.66 g, 16.3 mmol). The mixture was heated at 90° C. for 18 h then allowed to cool to room temperature (rt). Water was added and the mixture was extracted with DCM. Purification by FCC provided the desired product (3.23 g, 100%). 1H NMR (400 MHz, CDCl3): 8.21 (dd, J=2.5, 0.8 Hz, 1H), 7.81 (dd, J=8.3, 3.0 Hz, 1H), 7.45 (d, J=8.8 Hz, 1H), 7.26 (d, J=1.5 Hz, 1H), 7.00 (dd, J=9.0, 2.5 Hz, 1H), 6.88 (dd, J=8.8, 0.8 Hz, 1H).

Workup

  1. temperatureto cool to room temperature (rt)
  2. extractionthe mixture was extracted with DCM
  3. customPurification by FCC

Sources & evidence

ORD record
ord-a83725eee48b4087a809c8b159898b04
Source dataset
uspto-grants-2014_01
Patent number
US08637520B2

Reaction notes

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