Ethanol → HCID 71236655, compound

HRID 920316Notes

Reaction equation

HRID 920316 reaction equation
[Cl:1][C:2]1[CH:18]=[CH:17][C:5]([O:6][C:7]2[CH:8]=[CH:9][C:10]([CH2:13][C:14]([OH:16])=[O:15])=[N:11][CH:12]=2)=[CH:4][C:3]=1[C:19]([F:22])([F:21])[F:20].S(=O)(=O)(O)O.[NH4+].[OH-].C(Cl)Cl.[CH2:33](O)[CH3:34]>>[Cl:1][C:2]1[CH:18]=[CH:17][C:5]([O:6][C:7]2[CH:8]=[CH:9][C:10]([CH2:13][C:14]([O:16][CH2:33][CH3:34])=[O:15])=[N:11][CH:12]=2)=[CH:4][C:3]=1[C:19]([F:22])([F:20])[F:21]

Participants

6

Reactant 5

HCID 702Ethanol2×HCID 1118Sulfuric AcidHCID 6344DichloromethaneHCID 14923Ammonium HydroxideHCID 71236646HCID 71236646, compound

Product 1

HCID 71236655HCID 71236655, compoundYield 79%

Conditions

Temperature
80 °C

Procedure

To a solution of 2-(5-(4-chloro-3-(trifluoromethyl)phenoxy)pyridin-2-yl)acetic acid (3 g, 5.61 mmol) in ethanol (30 mL) was added sulfuric acid (8 mL, 150 mmol) in ethanol (30 mL). The reaction mixture was stirred at 80° C. for 2 hr. Then 30 mL of 25% aqueous NH4OH solution and 50 mL CH2Cl2 were added to the reaction mixture. The organic layer was separated and dried over Na2SO4, and concentrated under reduced pressure to provide ethyl 2-(5-(4-chloro-3-(trifluoromethyl)phenoxy)pyridin-2-yl)acetate (2 g, 79%).

Workup

  1. customThe organic layer was separated
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-880dc9aaecc346abb986651d7c904665
Source dataset
uspto-grants-2016_03
Patent number
US09273054B2

Reaction notes

Loading…