1,2-Dibromoethane → N-[4-(2-bromo-ethoxy)-3-chloro-phenyl]-2-(2-chloro-4-trifluoromethyl-phenoxy)-acetamide

HRID 898541Notes

Reaction equation

HRID 898541 reaction equation
[Br:1][CH2:2][CH2:3]Br.[Cl:5][C:6]1[CH:7]=[C:8]([NH:13][C:14](=[O:28])[CH2:15][O:16][C:17]2[CH:22]=[CH:21][C:20]([C:23]([F:26])([F:25])[F:24])=[CH:19][C:18]=2[Cl:27])[CH:9]=[CH:10][C:11]=1[OH:12].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[Br:1][CH2:2][CH2:3][O:12][C:11]1[CH:10]=[CH:9][C:8]([NH:13][C:14](=[O:28])[CH2:15][O:16][C:17]2[CH:22]=[CH:21][C:20]([C:23]([F:24])([F:25])[F:26])=[CH:19][C:18]=2[Cl:27])=[CH:7][C:6]=1[Cl:5]

Participants

5

Reactant 3

HCID 78391,2-DibromoethaneHCID 11430Potassium CarbonateHCID 68875945N-(3-chloro-4-hydroxy-phenyl)-2-(2-chloro-4-trifluoromethyl-phenoxy)-acetamide

Product 1

HCID 59691643N-[4-(2-bromo-ethoxy)-3-chloro-phenyl]-2-(2-chloro-4-trifluoromethyl-phenoxy)-acetamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of 3.66 mL (41.56 mmol) 1,2-dibromoethane in 5 mL DMF was slowly added at RT to a suspension of 1.580 g (4.156 mmol) N-(3-chloro-4-hydroxy-phenyl)-2-(2-chloro-4-trifluoromethyl-phenoxy)-acetamide and 2.880 g (8.310 mmol) potassium carbonate in 20 mL DMF and the mixture was stirred for 2.5 h. The reaction mixture was evaporated down i. vac. and diluted with EtOAc . The org. phase was washed with water and saturated aqueous NaCl, dried over magnesium sulphate and evaporated down i. vac. Column chromatography (silica gel, petroleum ether→dichloromethane) yielded the product.

Workup

  1. customThe reaction mixture was evaporated down i
  2. additionand diluted with EtOAc
  3. washphase was washed with water and saturated aqueous NaCl
  4. dry with materialdried over magnesium sulphate
  5. customevaporated down i
  6. customColumn chromatography (silica gel, petroleum ether→dichloromethane) yielded the product

Sources & evidence

ORD record
ord-6e3d9b598585439a8537dd7b84c3654c
Source dataset
uspto-grants-2008_04
Patent number
US07351719B2

Reaction notes

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