Benzenesulfonyl chloride → Benzene, 1-bromo-4-(phenylsulfonyl)- (9CI)

HRID 1726879Notes

Reaction equation

HRID 1726879 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:8]1([S:14](Cl)(=[O:16])=[O:15])[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[Cl-].[In+3].[Cl-].[Cl-].FC(F)(F)S(O)(=O)=O.[OH-].[Na+]>FC(F)(F)C(O)=O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([S:14]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)(=[O:16])=[O:15])=[CH:4][CH:3]=1

Participants

7

Reactant 5

HCID 7369Benzenesulfonyl chlorideHCID 7961BromobenzeneHCID 14798Sodium HydroxideHCID 62406Trifluoromethanesulfonic acidHCID 159675indium(III)chloride

Product 1

HCID 89970Benzene, 1-bromo-4-(phenylsulfonyl)- (9CI)

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of 199 μl of bromobenzene (1.88 mmol) and 361 μl of benzenesulphonyl chloride (2.83 mmol) in 4 ml of trifluoroacetic acid there are added, in succession, 83 mg of indium chloride (0.376 mmol) and then, dropwise, 25 μl of trifluoromethanesulphonic acid. The reaction mixture is stirred for 2 hours at 70° C. and is then returned to ambient temperature and diluted with ice-cold water. After rendering alkaline to pH 10 by adding concentrated sodium hydroxide solution, the reaction mixture is extracted with CH2Cl2. The organic phases are collected, washed with saturated NaCl, dried (MgSO4) and evaporated under reduced pressure to yield the title product in the form of a white solid.

Workup

  1. customis then returned to ambient temperature
  2. additiondiluted with ice-cold water
  3. extractionthe reaction mixture is extracted with CH2Cl2
  4. customThe organic phases are collected
  5. washwashed with saturated NaCl
  6. dry with materialdried (MgSO4)
  7. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-26e8394af0c54c0cbb675c1ea03fe974
Source dataset
uspto-grants-2009_02
Patent number
US07494994B2

Reaction notes

Loading…