Propargyl bromide → HCID 19753467, compound

HRID 483686Notes

Reaction equation

HRID 483686 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[S:11]([OH:13])=[O:12].Br[CH2:15][C:16]#[CH:17].C1COCC1>O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[S:11]([CH2:17][C:16]#[CH:15])(=[O:13])=[O:12]

Participants

5

Reactant 3

HCID 7842Propargyl bromideHCID 8028TetrahydrofuranHCID 1115232-Chloro-5-nitrobenzenesulphinic acid

Product 1

HCID 19753467HCID 19753467, compoundYield 73.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

110.7 g (0.5 mol) of 2-chloro-5-nitrobenzenesulfinic acid were dissolved in 500 ml of water at pH 6.5 and the solution was added to a solution of 65.5 g (0.55 mol) of 3-bromoprop-1-yne and 100 ml of THF. The reaction mixture was then heated to 40°-50° C. After the reaction had ended (check by TLC), the reaction product was extracted with 1.5 l of ethyl acetate, and the organic phase was neutralized and dried over sodium sulfate. The solvent was evaporated off to leave 95 g of 2-chloro-5-nitro-1-(prop-1-yn-3-ylsulfonyl)benzene (melting point 238°-241° C.). ##STR28##

Workup

  1. temperatureThe reaction mixture was then heated to 40°-50° C
  2. extractionthe reaction product was extracted with 1.5 l of ethyl acetate
  3. dry with materialdried over sodium sulfate
  4. customThe solvent was evaporated off

Sources & evidence

ORD record
ord-f43c9b6a80084eb6a3b02ba1cf40c9e5
Source dataset
uspto-grants-1993_07
Patent number
US05225595

Reaction notes

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