Ethanol → HCID 71236664, compound

HRID 920358Notes

Reaction equation

HRID 920358 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:16]=[CH:17][C:18]=1[F:19])[O:5][C:6]1[N:11]=[CH:10][C:9]([CH2:12][C:13]#N)=[CH:8][C:7]=1[F:15].[CH3:20][CH2:21][OH:22].S(=O)(=O)(O)[OH:24]>>[F:1][C:2]1[CH:3]=[C:4]([CH:16]=[CH:17][C:18]=1[F:19])[O:5][C:6]1[N:11]=[CH:10][C:9]([CH2:12][C:13]([O:22][CH2:21][CH3:20])=[O:24])=[CH:8][C:7]=1[F:15]

Participants

4

Reactant 3

HCID 702EthanolHCID 1118Sulfuric AcidHCID 71236677HCID 71236677, compound

Product 1

HCID 71236664HCID 71236664, compoundYield 99.7%

Conditions

Temperature
80 °C

Procedure

To 2-(6-(3,4-difluorophenoxy)-5-fluoropyridin-3-yl)acetonitrile (3 g, 9.99 mmol) and EtOH (30 ml, 514 mmol) was added 18 M sulfuric acid (10 ml, 180 mmol). The reaction mixture was stirred at 80° C. for 2 hr., and then was concentrated under reduced pressure. To the residue was added 50 mL of concentrated ammonia solution and 100 mL of CH2Cl2. The organic layer was separated and dried over Na2SO4, and then concentrated under reduced pressure to give ethyl 2-(6-(3,4-difluorophenoxy)-5-fluoropyridin-3-yl)acetate (3.1 g, 67.8%).

Workup

  1. concentration, and then was concentrated under reduced pressure
  2. additionTo the residue was added 50 mL of concentrated ammonia solution and 100 mL of CH2Cl2
  3. customThe organic layer was separated
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-caac41c513394147ab44154ba7131ed8
Source dataset
uspto-grants-2016_03
Patent number
US09273054B2

Reaction notes

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