Water → HCID 86694109, compound

HRID 707229Notes

Reaction equation

HRID 707229 reaction equation
[Cl:1][C:2]1[C:7]([C:8]2([C:11]#N)[CH2:10][CH2:9]2)=[CH:6][C:5]([F:13])=[CH:4][N:3]=1.C(OCC)(=[O:16])C.[OH2:20]>S(=O)(=O)(O)O>[Cl:1][C:2]1[C:7]([C:8]2([C:11]([OH:16])=[O:20])[CH2:10][CH2:9]2)=[CH:6][C:5]([F:13])=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 8857Ethyl AcetateHCID 86694105HCID 86694105, compound2×

Product 1

HCID 86694109HCID 86694109, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Conditions

Temperature
105 °C

Procedure

1-(2-chloro-5-fluoropyridin-3-yl)cyclopropanecarbonitrile (intermediate 16, 0.400 g, 2.034 mmol) was dissolved in a mixture of water (6 mL) and concentrated sulfuric acid (6 mL). The reaction was heated at 105° C. and stirred for 3½ hours. The reaction was cooled and ice (˜200 mL) and ethyl acetate (200 mL) were added. The pH was carefully adjusted to about 9 and the phases separated. The organic was discarded and the aqueous was reacidified to about pH 1 using 5 N hydrochloric acid. It was extracted with ethyl acetate (2×300 mL). The combined organic layers were dried with magnesium sulfate and evaporated to dryness under reduced pressure. The crude 1-(2-chloro-5-fluoropyridin-3-yl)cyclopropanecarboxylic acid (0.402 g, 1.864 mmol, 92% yield) was used without further purification.

Workup

  1. temperatureThe reaction was cooled
  2. customthe phases separated
  3. extractionIt was extracted with ethyl acetate (2×300 mL)
  4. dry with materialThe combined organic layers were dried with magnesium sulfate
  5. customevaporated to dryness under reduced pressure

Sources & evidence

ORD record
ord-9455d35de31d45518a85f4ec2d671ac2
Source dataset
uspto-grants-2015_11
Patent number
US09174992B2

Reaction notes

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