Hydrochloric Acid → HCID 86639397, compound

HRID 1673187Notes

Reaction equation

HRID 1673187 reaction equation
[CH2:1]([O:4][C:5](=[O:15])[C:6]1[CH:11]=[C:10]([F:12])[C:9](F)=[CH:8][C:7]=1[Cl:14])[C:2]#[CH:3].[CH2:16]([OH:19])[C:17]#[CH:18].[H-].[Na+].Cl>CN(C=O)C>[CH2:1]([O:4][C:5](=[O:15])[C:6]1[CH:11]=[C:10]([F:12])[C:9]([O:19][CH2:16][C:17]#[CH:18])=[CH:8][C:7]=1[Cl:14])[C:2]#[CH:3]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7859Propargyl alcoholHCID 24758Sodium hydrideHCID 86639398HCID 86639398, compound

Product 1

HCID 86639397HCID 86639397, compoundYield 129.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixed solution of 150 ml of DMF, 12.7 g of 2-chloro-4,5-difluorobenzoic acid 2-propynyl ester and 3.4 g of propargyl alcohol, 2.4 g of 60% sodium hydride (oily) was added under ice cooling. After stirring at room temperature overnight, the reaction mixture was added with hydrochloric acid and extracted with ethyl acetate. The obtained organic layer was washed in turn with water and saturated brine, dried over magnesium sulfate and then concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography, and 19 g of 2-chloro-5-fluoro-4-(2-propynyloxy)benzoic acid 2-propynyl ester was obtained.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe obtained organic layer was washed in turn with water and saturated brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-118a2b1bc5b847fb865c3b5a8a955fbe
Source dataset
uspto-grants-2011_08
Patent number
US07999136B2

Reaction notes

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