p-Toluenesulfonic acid → 2-Nitro-4-(1-pyrrolyl)fluorobenzene

HRID 1075447Notes

Reaction equation

HRID 1075447 reaction equation
[F:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10].CO[CH:14]1[CH2:18][CH2:17][CH:16](OC)O1.CC1C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[N+:9]([C:3]1[CH:4]=[C:5]([N:6]2[CH:14]=[CH:18][CH:17]=[CH:16]2)[CH:7]=[CH:8][C:2]=1[F:1])([O-:11])=[O:10]

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 677684-Fluoro-3-nitroanilineHCID 790982,5-Dimethoxytetrahydrofuran

Product 1

HCID 541021862-Nitro-4-(1-pyrrolyl)fluorobenzene

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a suspension of 4-fluoro-3-nitroaniline (20g, 0.13mol) in toluene (200mi) is added 2,5-dimethoxytetrahydrofuran (33ml, 0.26mol) and a catalytic amount of pTSA. The mixture is refluxed for 2.5 hours. After cooling the solvent is removed by evaporation and the residue is purified by column chromatography on silica gel using a mixture of ethyl acetate and petroleum ether (1:1) as the eluent. Yield: 23.1g (87%). Mp 79-81° C.

Workup

  1. temperatureThe mixture is refluxed for 2.5 hours
  2. temperatureAfter cooling the solvent
  3. customis removed by evaporation
  4. customthe residue is purified by column chromatography on silica gel using
  5. additiona mixture of ethyl acetate and petroleum ether (1:1) as the eluent

Sources & evidence

ORD record
ord-0961fcfc81a14fcfaf9cb8e1dcf8de2d
Source dataset
uspto-grants-1999_05
Patent number
US05902813

Reaction notes

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