4-Nitrophenol → HCID 18704822, compound

HRID 343384Notes

Reaction equation

HRID 343384 reaction equation
[I:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8](Cl)(=[O:10])=[O:9].[N+:12]([C:15]1[CH:20]=[CH:19][C:18]([OH:21])=[CH:17][CH:16]=1)([O-:14])=[O:13]>N1C=CC=CC=1>[I:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8]([O:21][C:18]1[CH:19]=[CH:20][C:15]([N+:12]([O-:14])=[O:13])=[CH:16][CH:17]=1)(=[O:10])=[O:9]

Participants

4

Reactant 2

HCID 9804-NitrophenolHCID 6274002-Iodobenzene-1-sulfonyl chloride

Product 1

HCID 18704822HCID 18704822, compoundYield 70.6%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of 2-iodobenzenesulphonyl chloride (obtained as described in J. Org. Chem. 1977, 42, 3265) (8.28 g) and 4-nitrophenol (3.81 g) in pyridine (50 ml) was heated at 100° C. for 3 hours. Volatile material was removed by evaporation and water (200 ml) was added to the residue. The mixture was extracted with ethyl acetate (2×200 ml) and the combined extracts were washed with 1M hydrochloric acid (2×200 ml) and dried (MgSO4). Solvent was removed by evaporation and the residue was recrystallised from a mixture of ethyl acetate and hexane to give 4-nitrophenyl 2-iodobenzenesulphonate (7.83 g), m.p. 131°-133° C.; mass spectrum (+ve CI): 405 (M+).

Workup

  1. customVolatile material was removed by evaporation and water (200 ml)
  2. additionwas added to the residue
  3. extractionThe mixture was extracted with ethyl acetate (2×200 ml)
  4. washthe combined extracts were washed with 1M hydrochloric acid (2×200 ml)
  5. dry with materialdried (MgSO4)
  6. customSolvent was removed by evaporation
  7. customthe residue was recrystallised from a mixture of ethyl acetate and hexane

Sources & evidence

ORD record
ord-6adea5717bd3495090fa6d45f2239a88
Source dataset
uspto-grants-1999_01
Patent number
US05861401

Reaction notes

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