Chlorosulfonic acid → 3-Bromo-4-(trifluoromethoxy)benzenesulfonyl chloride

HRID 870343Notes

Reaction equation

HRID 870343 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[O:8][C:9]([F:12])([F:11])[F:10].[Cl:13][S:14](O)(=[O:16])=[O:15]>ClCCl.CCCCCCC.ClCCl>[Br:1][C:2]1[CH:7]=[C:6]([S:14]([Cl:13])(=[O:16])=[O:15])[CH:5]=[CH:4][C:3]=1[O:8][C:9]([F:11])([F:10])[F:12]

Participants

5

Reactant 2

HCID 24638Chlorosulfonic acidHCID 27772661-Bromo-2-(trifluoromethoxy)benzene

Product 1

HCID 509980203-Bromo-4-(trifluoromethoxy)benzenesulfonyl chlorideYield 77.7%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent3×HCID 21907733Dichloromethane heptaneSolvent

Procedure

2.0 g of 1-bromo-2-(trifluoro-methoxy)benzene (8.3 mmol) were dissolved in 30 ml of dichloromethane. At 0-5° C., 1.06 g of chlorosulfonic acid (9.13 mmol), dissolved in 3 ml of dichloromethane, were added dropwise. The reaction mixture was stirred for 30 min at room temperature. Additional 5.5 equivalents of chlorosulfonic in dichloromethane were added to drive the reaction to completion. Standard work-up was followed and silica gel chromatography with n-heptane-dichloromethane (6:4) as eluent gave 2.19 g of the title compound.

Workup

  1. additionwere added dropwise
  2. customthe reaction to completion

Sources & evidence

ORD record
ord-a7097275b96e462289c2007119b09759
Source dataset
uspto-grants-2015_03
Patent number
US08969552B2

Reaction notes

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