Propargyl bromide → Propargyl 3-chloro-4,5-dipropargyloxybenzoate

HRID 1708979Notes

Reaction equation

HRID 1708979 reaction equation
[H-].[Na+].[Cl:3][C:4]1[CH:5]=[C:6]([CH:10]=[C:11]([O:17][CH2:18][C:19]#[CH:20])[C:12]=1[O:13][CH2:14][C:15]#[CH:16])[C:7]([OH:9])=[O:8].[CH2:21](Br)[C:22]#[CH:23]>CN(C)C=O>[Cl:3][C:4]1[CH:5]=[C:6]([CH:10]=[C:11]([O:17][CH2:18][C:19]#[CH:20])[C:12]=1[O:13][CH2:14][C:15]#[CH:16])[C:7]([O:9][CH2:23][C:22]#[CH:21])=[O:8]

Participants

5

Reactant 3

HCID 7842Propargyl bromideHCID 24758Sodium hydrideHCID 141303193-Chloro-4,5-dipropargyloxybenzoic acid

Product 1

HCID 14130322Propargyl 3-chloro-4,5-dipropargyloxybenzoateYield 60%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (0.23 g; 60% dispersion in mineral oil) was added to a solution of 3-chloro-4,5-dipropargyloxybenzoic acid (1.50 g) in N,N-dimethylformamide (50 ml) at 0° C., followed by stirring at room temperature for 1 hour. Propargyl bromide (0.80 g) was added thereto, and the resultant mixture was stirred at 90° C. for 5 minutes, poured into ice-water and extracted with ethyl acetate. The extract was washed with an aqueous potassium carbonate solution, dried over magnesium sulfate and concentrated under reduced pressure. The residue was subjected to silica gel chromatography using toluene as an eluent to give propargyl 3-chloro-4,5-dipropargyloxybenzoate (1.03 g). m.p. 98°-99° C.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with an aqueous potassium carbonate solution
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-616c404a94634bc58fa03101af971bd2
Source dataset
uspto-grants-1990_08
Patent number
US04946865

Reaction notes

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