Acetonitrile → 1-Bromo-2-[4-(methanesulfonyl)phenyl]-6-methoxynaphthalene

HRID 748975Notes

Reaction equation

HRID 748975 reaction equation
[Br:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:12][CH3:13])=[CH:9][CH:10]=2)[CH2:5][CH2:4][C:3]=1[C:14]1[CH:19]=[CH:18][C:17]([S:20]([CH3:23])(=[O:22])=[O:21])=[CH:16][CH:15]=1.ClC1C(=O)C(C#N)=C(C#N)C(=O)C=1Cl.C(#N)C.[OH-].[Na+]>C1COCC1>[Br:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:12][CH3:13])=[CH:9][CH:10]=2)[CH:5]=[CH:4][C:3]=1[C:14]1[CH:19]=[CH:18][C:17]([S:20]([CH3:23])(=[O:22])=[O:21])=[CH:16][CH:15]=1

Participants

6

Reactant 4

HCID 6342AcetonitrileHCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinone2×HCID 14798Sodium HydroxideHCID 68516997HCID 68516997, compound

Product 1

HCID 685183171-Bromo-2-[4-(methanesulfonyl)phenyl]-6-methoxynaphthalene

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Combine 1-bromo-2-(4-methanesulfonylphenyl)-3,4-dihydro-6-methoxynaphthalene and 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ, 1.8 equiv.) in 10 volumes acetonitrile and 5 volumes of THF. Under nitrogen atmosphere, heat reaction contents to 73-75° C. Monitor reaction progress by GC analysis until reaction, completion. Additional DDQ (0.2-0.3 equiv.) may be required for reaction completion. Cool contents to ambient temperature and add 10 volumes 1 N sodium hydroxide. Stir for approximately 1 hour and filter. Rinse filter cake with 2 volumes water, 3×5 volumes 50% acetonitrile/water and finally 3 volumes methanol. Vacuum dry the filter cake at 65° C. to give the title compound.

Workup

  1. temperatureUnder nitrogen atmosphere, heat
  2. customreaction contents to 73-75° C
  3. customMonitor reaction progress by GC analysis
  4. customuntil reaction, completion
  5. filtrationfilter
  6. washRinse
  7. filtrationfilter cake with 2 volumes water, 3×5 volumes 50% acetonitrile/water and finally 3 volumes methanol
  8. customVacuum dry the filter cake at 65° C.

Sources & evidence

ORD record
ord-b6d4a5d4133b493d8297d84eb9ecdc73
Source dataset
uspto-grants-2008_07
Patent number
US07399867B2

Reaction notes

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