Chlorosulfonic acid → [2-(4-Fluorophenoxy)phenyl]sulfonyl chloride

HRID 2265876Notes

Reaction equation

HRID 2265876 reaction equation
[Cl:1][S:2]([OH:5])(=O)=[O:3].[F:6][C:7]1[CH:19]=[CH:18][C:10]([O:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:9][CH:8]=1>ClCCl>[F:6][C:7]1[CH:19]=[CH:18][C:10]([O:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[S:2]([Cl:1])(=[O:5])=[O:3])=[CH:9][CH:8]=1

Participants

4

Reactant 2

HCID 24638Chlorosulfonic acidHCID 676141-Fluoro-4-phenoxybenzene

Product 1

HCID 5187142[2-(4-Fluorophenoxy)phenyl]sulfonyl chloride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

16.1 g (0.138 mol) of chlorosulfonic acid are slowly added dropwise to a solution of 13.05 g of 4-fluorophenoxybenzene (0.069 mol) cooled to 0° C. After the addition is complete, the mixture is stirred at room temperature for a further 4 hours. For work up, 50 ml of dichloromethane are added, and the mixture is washed once with H2O. The aqueous phase is separated off and extracted twice more with 50 ml of dichloromethane each time. The combined organic phases are dried with MgSO4 and concentrated, resulting in the title compound as a colorless solid. Yield: 11.03 g; 60%.

Workup

  1. additionAfter the addition
  2. washthe mixture is washed once with H2O
  3. customThe aqueous phase is separated off
  4. extractionextracted twice more with 50 ml of dichloromethane each time
  5. dry with materialThe combined organic phases are dried with MgSO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-eb20f46957c549419a0abe64f464ee33
Source dataset
uspto-grants-2010_12
Patent number
US07858619B2

Reaction notes

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