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Chlorosulfonic acid → 4-Fluoro-3-iodobenzenesulfonyl chloride

HRID 2283651
Notes
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Reaction equation

HRID 2283651 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[I:8].[Cl:9][S:10](O)(=[O:12])=[O:11]>CCCCCCC>[F:1][C:2]1[C:3]([I:8])=[CH:4][C:5]([S:10]([Cl:9])(=[O:12])=[O:11])=[CH:6][CH:7]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 24638Chlorosulfonic acidHCID 676731-Fluoro-2-iodobenzene

Product 1

HCID 866823704-Fluoro-3-iodobenzenesulfonyl chloride

Reagents, catalysts & solvents 1

HCID 8900HeptaneSolvent

Procedure

2-Fluoroiodobenzene (0.58 mL, 5.0 mmol) was added dropwise to chlorosulfonic acid (1.66 mL, 25 mmol) at 0° C. The reaction mixture was allowed to warm to ambient temperature and stirred for 2 hours. The reaction mixture was poured into ice and the mixture was extracted with dichloromethane (3×30 mL). The combined organic layer was dried over magnesium sulfate and concentrated in vacuo to obtain a crude residue. The crude residue was dissolved in heptane (100 mL) and the suspension was filtered. The filtrate was concentrated in vacuo to afford the title compound.

On this pageParticipantsProcedureWorkupSources & evidenceReaction notes

Workup

  1. additionThe reaction mixture was poured into ice
  2. extractionthe mixture was extracted with dichloromethane (3×30 mL)
  3. dry with materialThe combined organic layer was dried over magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. customto obtain a crude residue
  6. filtrationthe suspension was filtered
  7. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-8047d219d85145978962a3fe58a6e321
Source dataset
uspto-grants-2015_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09145407B2

Reaction notes

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