Benzene → 4-bromo-2-chloro-1-(phenylsulfonyl)Benzene

HRID 1972361Notes

Reaction equation

HRID 1972361 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([S:8](Cl)(=[O:10])=[O:9])=[C:4]([Cl:12])[CH:3]=1.[CH:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.CCO>O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)(=[O:10])=[O:9])=[C:4]([Cl:12])[CH:3]=1

Participants

5

Reactant 3

HCID 241BenzeneHCID 702EthanolHCID 27347664-Bromo-2-chlorobenzenesulfonyl chloride

Product 1

HCID 665825034-bromo-2-chloro-1-(phenylsulfonyl)Benzene

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A 500 mL round-bottomed flask was charged with 4-bromo-2-chlorobenzene-1-sulfonyl chloride (10.0 g, 34.5 mmol, Sigma-Aldrich, St. Louis, Mo.), ferric chloride (2.80 g, 17.2 mmol), and 200 mL of benzene. The mixture was heated at reflux for 12 h then diluted with water (100 mL) and extracted with CH2Cl2 (2×300 mL). The combined organic layers were dried (MgSO4) and concentrated to give a brown solid that was slurried with EtOH (100 mL) to give 4-bromo-2-chloro-1-(phenylsulfonyl)benzene (7.50 g).

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 12 h
  3. extractionextracted with CH2Cl2 (2×300 mL)
  4. dry with materialThe combined organic layers were dried (MgSO4)
  5. concentrationconcentrated
  6. customto give a brown solid that

Sources & evidence

ORD record
ord-7cda62b32a184c47ba54d4bb5d89f624
Source dataset
uspto-grants-2013_04
Patent number
US08431563B2

Reaction notes

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