2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → 6-Fluoronaphthalen-1-yl trifluoromethanesulfonate

HRID 2056727Notes

Reaction equation

HRID 2056727 reaction equation
[F:1][C:2]([F:19])([F:18])[S:3]([O:6][C:7]1[C:16]2[C:11](=[CH:12][C:13]([F:17])=[CH:14][CH:15]=2)[CH2:10][CH2:9][CH:8]=1)(=[O:5])=[O:4].ClC1C(=O)C(C#N)=C(C#N)C(=O)C=1Cl>O1CCOCC1>[F:19][C:2]([F:1])([F:18])[S:3]([O:6][C:7]1[C:16]2[C:11](=[CH:12][C:13]([F:17])=[CH:14][CH:15]=2)[CH:10]=[CH:9][CH:8]=1)(=[O:5])=[O:4]

Participants

4

Reactant 2

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 17933618HCID 17933618, compound

Product 1

HCID 179336066-Fluoronaphthalen-1-yl trifluoromethanesulfonate

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of 6-fluoro-3,4-dihydro-1-naphthalenyl trifluoromethane sulfonate (0.77 g, 2.8 mmol) in dioxan (15 mL) was added 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (0.95 g, 4.2 mmol) and the reaction mixture heated under reflux for 18 h. The solvent was removed in vacuo and the crude product purified by column chromatography on silica, eluting with hexane, to yield 6-fluoro-1-naphthyl trifluoromethanesulfonate as a white solid.

Workup

  1. temperaturethe reaction mixture heated
  2. temperatureunder reflux for 18 h
  3. customThe solvent was removed in vacuo
  4. customthe crude product purified by column chromatography on silica
  5. washeluting with hexane

Sources & evidence

ORD record
ord-cd3ca326997d43d0a1fc37127e3e075f
Source dataset
uspto-grants-2008_02
Patent number
US07335660B2

Reaction notes

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