5-Fluoro-2-nitrotoluene → HCID 19692290, compound

HRID 230843Notes

Reaction equation

HRID 230843 reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[C:4]([CH3:11])[CH:3]=1.[C:12]1([S:18]([O-:20])=[O:19])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[Na+]>CN(C)C(=O)C>[C:12]1([S:18]([C:2]2[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[C:4]([CH3:11])[CH:3]=2)(=[O:20])=[O:19])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

4

Reactant 2

HCID 949565-Fluoro-2-nitrotolueneHCID 2723840Benzenesulfinic acid, sodium salt

Product 1

HCID 19692290HCID 19692290, compoundYield 75.3%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

4-Fluoro-2-methyl-1-nitrobenzene (2.6 g) (available from Aldrich) and sodium benzenesulfinate (3.0 g) (available from Aldrich) were heated in N,N-dimethylacetamide (40 ml) at 50° C. for 16 h. After cooling the mixture was filtered, the filtrate collected and the solvent removed in vacuo. The residue was triturated with cyclohexane and the resultant precipitate collected by filtration to give the title compound as a white solid (3.5 g).

Workup

  1. temperatureAfter cooling the mixture
  2. filtrationwas filtered
  3. customthe filtrate collected
  4. customthe solvent removed in vacuo
  5. customThe residue was triturated with cyclohexane
  6. filtrationthe resultant precipitate collected by filtration

Sources & evidence

ORD record
ord-ba26fb4d340b46a78c6bac72ecfa8ad6
Source dataset
uspto-grants-2009_07
Patent number
US07566786B2

Reaction notes

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