Propargyl bromide → 1-Nitro-3-(prop-2-yne-1-sulfonyl)benzene

HRID 483687Notes

Reaction equation

HRID 483687 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([S:10]([OH:12])=[O:11])[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].Br[CH2:14][C:15]#[CH:16].C1COCC1>O>[N+:1]([C:4]1[CH:5]=[C:6]([S:10]([CH2:16][C:15]#[CH:14])(=[O:12])=[O:11])[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 7842Propargyl bromideHCID 8028TetrahydrofuranHCID 6913772HCID 6913772, compound

Product 1

HCID 141695931-Nitro-3-(prop-2-yne-1-sulfonyl)benzeneYield 53.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

93.5 g (0.5 mol) of 3-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 of 3-bromo-prop-1-yne and 70 ml of THF. The reaction mixture was heated at 40°-50° C. until the reaction had ended (check by TLC). The reaction product was extracted with about 1.5 l of ethyl acetate, and the organic phase was neutralized and dried over sodium sulfate. The solvent was evaporated off to leave 60 g of 3-nitro-1-(prop-1-yn-3-ylsulfonyl)benzene (melting point 250°-255° C.). ##STR29##

Workup

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

Sources & evidence

ORD record
ord-0377a72066f94049b27a9f1b4e74a55a
Source dataset
uspto-grants-1993_07
Patent number
US05225595

Reaction notes

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