N-methyl-2-pyrrolidone → 1-Fluoro-2-iodo-3-nitrobenzene

HRID 1722452Notes

Reaction equation

HRID 1722452 reaction equation
FC(F)(F)S(O[C:7]1[C:12]([N+:13]([O-:15])=[O:14])=[CH:11][CH:10]=[CH:9][C:8]=1[F:16])(=O)=O.[I-:19].[Li+].CN1CCCC1=O>O>[I:19][C:7]1[C:8]([F:16])=[CH:9][CH:10]=[CH:11][C:12]=1[N+:13]([O-:15])=[O:14]

Participants

5

Reactant 3

HCID 13387N-methyl-2-pyrrolidoneHCID 66321Lithium iodideHCID 200290852-Fluoro-6-nitrophenyl Trifluoromethanesulfonate

Product 1

HCID 234335971-Fluoro-2-iodo-3-nitrobenzeneYield 47%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture consisting of 2-fluoro-6-nitrophenyl trifluoromethanesulfonate (62.0 g, 0.215 mol), lithium iodide (60 g, 0.451 mol) and 1-methyl-2-pyrrolidinone (400 mL) was heated with stirring at 130°-132° C. (oil bath temperature) for 18 hours. Upon cooling it was poured into water (1200 mL) and extracted with diethyl ether. The combined extracts were washed with 1N NaOH, water and with brine. The solution was dried (MgSO4), filtered, and concentrated in vacuo to give 27.0 g of the title compound as a brown-colored solid title compound (m.p. 54°-57° C.).

Workup

  1. temperaturewas heated
  2. temperatureUpon cooling it
  3. extractionextracted with diethyl ether
  4. washThe combined extracts were washed with 1N NaOH, water and with brine
  5. dry with materialThe solution was dried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f5c8892df57b4e93b632b6f9ba793781
Source dataset
uspto-grants-1989_08
Patent number
US04855445

Reaction notes

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