Sodium Carbonate → 1,2,3,4-Tetrafluoro-5-(4-fluorophenyl)-6-[4-(methylthio)phenyl]benzene

HRID 1839934Notes

Reaction equation

HRID 1839934 reaction equation
Br[C:2]1[C:7]([F:8])=[C:6]([F:9])[C:5]([F:10])=[C:4]([F:11])[C:3]=1Br.[F:13][C:14]1[CH:19]=[CH:18][C:17](B(O)O)=[CH:16][CH:15]=1.[CH3:23][S:24][C:25]1[CH:30]=[CH:29][C:28](B(O)O)=[CH:27][CH:26]=1.C([O-])([O-])=O.[Na+].[Na+]>C1(C)C=CC=CC=1.C(O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[F:8][C:7]1[C:2]([C:28]2[CH:29]=[CH:30][C:25]([S:24][CH3:23])=[CH:26][CH:27]=2)=[C:3]([C:17]2[CH:18]=[CH:19][C:14]([F:13])=[CH:15][CH:16]=2)[C:4]([F:11])=[C:5]([F:10])[C:6]=1[F:9]

Participants

8

Reactant 4

HCID 10340Sodium CarbonateHCID 700071,2-Dibromo-3,4,5,6-tetrafluorobenzeneHCID 2856454-Fluorophenylboronic acidHCID 27339594-(Methylthio)phenylboronic acid

Product 1

HCID 104991151,2,3,4-Tetrafluoro-5-(4-fluorophenyl)-6-[4-(methylthio)phenyl]benzeneYield 126.1%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolventHCID 1140TolueneSolvent

Procedure

Under nitrogen, 1 g of Pd(PPh3)4 was added to a stirred solution of 4.85 g (15.8 mmol) of 1,2-dibromo-3,4,5,6-tetrafluorobenzene (Aldrich), 2.65 g (18.9 mmol) of 4-fluorophenylboronic acid, and 3.17 g (18.9 mmol) of 4-methylthiophenylboronic acid (Example 1, Step 2) in 80 mL of toluene, 50 mL of ethanol, and 35 mL of 2M Na2CO3. After vigorous stirring at reflux overnight, the solvent was removed in vacuo. The residue was dissolved in ethyl acetate, washed water, and dried over Na2SO4. Concentration in vacuo gave 7.3 g of 1,2,3,4-tetrafluoro-5-(4-fluorophenyl)-6-[4-(methylthio)phenyl]benzene as a yellow oil which was used without further purification.

Workup

  1. temperatureat reflux overnight
  2. customthe solvent was removed in vacuo
  3. dissolutionThe residue was dissolved in ethyl acetate
  4. washwashed water
  5. dry with materialdried over Na2SO4
  6. concentrationConcentration in vacuo

Sources & evidence

ORD record
ord-414a4b6d223142559551f3423b06fd4e
Source dataset
uspto-grants-2004_01
Patent number
US06677488B2

Reaction notes

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