Hydrochloric Acid → 2-Bromo-5-(methylsulphonyl)aniline

HRID 340193Notes

Reaction equation

HRID 340193 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([CH3:11])(=[O:10])=[O:9])=[CH:4][C:3]=1[N+:12]([O-])=O.Cl>C(O)C.[Fe]>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([CH3:11])(=[O:10])=[O:9])=[CH:4][C:3]=1[NH2:12]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 20603662-Bromo-5-methylsulfonylnitrobenzene

Product 1

HCID 265975132-Bromo-5-(methylsulphonyl)aniline

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 702EthanolSolvent

Procedure

A solution of 1-bromo-4-(methylsulfonyl)-2-nitrobenzene (1.0 eq.), iron powder (3.0 eq.), and concentrated HCl (1.04 eq.) were mixed together in ethanol (0.64 M) and heated to reflux. The reaction was stirred for 24 hours, and the solvent was evaporated. The resulting residue was diluted with ethyl acetate and saturated aqueous ammonium chloride solution. The aqueous layer was extracted three times with ethyl acetate, and the combined organic layers were washed with water, brine, dried over anhydrous MgSO4, and concentrated en vacuo. The crude material was purified by triturating in 1:1 hexane/ether to give a light yellow solid.

Workup

  1. temperatureheated to reflux
  2. customthe solvent was evaporated
  3. additionThe resulting residue was diluted with ethyl acetate and saturated aqueous ammonium chloride solution
  4. extractionThe aqueous layer was extracted three times with ethyl acetate
  5. washthe combined organic layers were washed with water, brine
  6. dry with materialdried over anhydrous MgSO4
  7. concentrationconcentrated en vacuo
  8. customThe crude material was purified
  9. customby triturating in 1:1 hexane/ether
  10. customto give a light yellow solid

Sources & evidence

ORD record
ord-87f6278c5290492991fbc10d08b8a5a1
Source dataset
uspto-grants-2014_11
Patent number
US08895577B2

Reaction notes

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