Nitromethane → Phenyl 2-(4-fluorophenyl)-2-nitroethanesulfonate

HRID 501250Notes

Reaction equation

HRID 501250 reaction equation
C[O-].[Na+].[N+:4](C)([O-:6])=[O:5].[F:8][C:9]1[CH:14]=[CH:13][C:12]([CH:15]=[CH:16][S:17]([O:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)(=[O:19])=[O:18])=[CH:11][CH:10]=1>CS(C)=O>[F:8][C:9]1[CH:10]=[CH:11][C:12]([CH:15]([N+:4]([O-:6])=[O:5])[CH2:16][S:17]([O:20][C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)(=[O:18])=[O:19])=[CH:13][CH:14]=1

Participants

5

Reactant 3

HCID 6375NitromethaneHCID 10942334Sodium MethoxideHCID 86243865Phenyl 2-(4-fluorophenyl)ethenesulfonate

Product 1

HCID 86616500Phenyl 2-(4-fluorophenyl)-2-nitroethanesulfonate

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

56.3 g of sodium methanolate were taken up in 1 l of DMSO and, at RT, 56.3 ml of nitromethane were added dropwise. The internal temperature rose to 40° C. during this. Then, at a temperature between 26° C. and 30° C., a solution of 145.0 g of phenyl 2-(4-fluorophenyl)ethenesulfonate in 1 l of DMSO was added dropwise. Stirring at RT for 1 hour was followed by leaving to stand at RT for 16 hours and then stirring at RT for a further 6 hours and 30 minutes. The reaction mixture was then poured into 8 kg of ice and extracted 5 times with 2 l of EA each time. After drying over Na2SO4, the solvent was removed in vacuo. Chromatography on silica gel with EA/HEP 1:5 afforded 77.35 g of a colorless oil.

Workup

  1. customrose to 40° C.
  2. customby leaving
  3. waitto stand at RT for 16 hours
  4. stirringstirring at RT for a further 6 hours and 30 minutes
  5. extractionextracted 5 times with 2 l of EA each time
  6. dry with materialAfter drying over Na2SO4
  7. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-7d4ac940eb414b05aefd3db1ef7593f2
Source dataset
uspto-grants-2010_08
Patent number
US07772262B2

Reaction notes

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