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Water → 1-(3,5-Difluoropyridin-2-yl)-2-(2-fluorophenyl)ethanone

HRID 570516
Notes
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Reaction equation

HRID 570516 reaction equation
[F:1][C:2]1[C:3]([C:9](=[O:22])[CH:10]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[F:21])C(OC)=O)=[N:4][CH:5]=[C:6]([F:8])[CH:7]=1.[Cl-].[Na+].O>CS(C)=O.C(OCC)(=O)C>[F:1][C:2]1[C:3]([C:9](=[O:22])[CH2:10][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[F:21])=[N:4][CH:5]=[C:6]([F:8])[CH:7]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 962WaterHCID 5234Sodium ChlorideHCID 66635086Methyl 3-(3,5-difluoropyridin-2-yl)-2-(2-fluorophenyl)-3-oxopropanoate

Product 1

HCID 666355431-(3,5-Difluoropyridin-2-yl)-2-(2-fluorophenyl)ethanone

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolvent
HCID 8857
Ethyl Acetate
Solvent

Conditions

Temperature
150 °C

Procedure

11.65 g (37.67 mmol) of the compound from Example 13A were initially charged in DMSO (37 ml). Subsequently, 2.42 g (41.44 mmol) of sodium chloride and water (7 ml) were added, and the mixture was stirred in a microwave at 150° C. for 30 min. The reaction mixture was diluted with ethyl acetate, and the organic phase was washed three times with water and once with saturated aqueous sodium chloride solution, dried over sodium sulphate, filtered and concentrated. This gave 9.07 g (89%, 85% of theory) of the desired compound in solid form, which was converted without further purification.

Workup

  1. washthe organic phase was washed three times with water
  2. dry with materialonce with saturated aqueous sodium chloride solution, dried over sodium sulphate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThis gave 9.07 g (89%, 85% of theory) of the desired compound in solid form, which was converted without further purification

Sources & evidence

ORD record
ord-88923dcd69e64635abe555c3cc4baaa8
Source dataset
uspto-grants-2015_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09023849B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes