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

HRID 2101671Notes

Reaction equation

HRID 2101671 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-29dfa5e9f73248e387b99922373b0022
Source dataset
uspto-grants-2009_08
Patent number
US07572915B2

Reaction notes

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