Dimethylformamide → 2-(4-Fluorobenzyloxy)ethyl 2-[4-(3,5-dichloro-2-pyridyloxy)phenoxy]propionate

HRID 325591Notes

Reaction equation

HRID 325591 reaction equation
[Na].[Cl:2][C:3]1[C:4]([O:10][C:11]2[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][CH:12]=2)=[N:5][CH:6]=[C:7]([Cl:9])[CH:8]=1.Cl[CH:19]([CH3:34])[C:20]([O:22][CH2:23][CH2:24][O:25][CH2:26][C:27]1[CH:32]=[CH:31][C:30]([F:33])=[CH:29][CH:28]=1)=[O:21].CN(C)C=O>O>[Cl:2][C:3]1[C:4]([O:10][C:11]2[CH:16]=[CH:15][C:14]([O:17][CH:19]([CH3:34])[C:20]([O:22][CH2:23][CH2:24][O:25][CH2:26][C:27]3[CH:28]=[CH:29][C:30]([F:33])=[CH:31][CH:32]=3)=[O:21])=[CH:13][CH:12]=2)=[N:5][CH:6]=[C:7]([Cl:9])[CH:8]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 132171142-(4-Fluorobenzyloxy)ethyl 2-chloropropionateHCID 704565004-(3,5-Dichloro-2-pyridyloxy)phenol sodium salt

Product 1

HCID 133416712-(4-Fluorobenzyloxy)ethyl 2-[4-(3,5-dichloro-2-pyridyloxy)phenoxy]propionate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

30.6 g of 4-(3,5-dichloro-2-pyridyloxy)phenol sodium salt and 30.5 g of 2-(4-fluorobenzyloxy)ethyl 2-chloropropionate were added to 100 ml of dimethylformamide, and the mixture was heated to 70° to 80° C. for 3 hours with stirring. After cooling to room temperature, the reaction solution was poured into 300 ml of water, then extracted with ether. The ether layer was washed successively with 1% strength by weight sodium hydroxide aqueous solution and water, followed by dehydration. Upon distilling off the ether, there were obtained 38 g of a pale yellow, viscous, oily end product, 2-(4-fluorobenzyloxy)ethyl 2-[4-(3,5-dichloro-2-pyridyloxy)phenoxy]propionate.

Workup

  1. temperaturethe mixture was heated to 70° to 80° C. for 3 hours
  2. extractionextracted with ether
  3. washThe ether layer was washed successively with 1% strength by weight sodium hydroxide aqueous solution and water
  4. distillationUpon distilling off the ether

Sources & evidence

ORD record
ord-ef703bbe53844a10b00ab9bd9d5f8f8d
Source dataset
uspto-grants-1984_04
Patent number
US04441913

Reaction notes

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