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

HRID 1839932Notes

Reaction equation

HRID 1839932 reaction equation
Br[C:2]1[CH:7]=[C:6]([F:8])[C:5]([F:9])=[CH:4][C:3]=1Br.[CH3:11][S:12][C:13]1[CH:18]=[CH:17][C:16](B(O)O)=[CH:15][CH:14]=1.[F:22][C:23]1[CH:28]=[CH:27][C:26](B(O)O)=[CH:25][CH:24]=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:6]1[CH:7]=[C:2]([C:16]2[CH:17]=[CH:18][C:13]([S:12][CH3:11])=[CH:14][CH:15]=2)[C:3]([C:26]2[CH:27]=[CH:28][C:23]([F:22])=[CH:24][CH:25]=2)=[CH:4][C:5]=1[F:9]

Participants

8

Reactant 4

HCID 10340Sodium CarbonateHCID 949491,2-Dibromo-4,5-difluorobenzeneHCID 2856454-Fluorophenylboronic acidHCID 27339594-(Methylthio)phenylboronic acid

Product 1

HCID 234513441,2-Difluoro-4-(4-fluorophenyl)-5-[4-(methylthio)phenyl]benzene

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolventHCID 1140TolueneSolvent

Procedure

Under nitrogen, 3 g (2.6 mmol) of Pd(PPh3)4 was added to a stirred solution of 5.0 g (18 mmol) of 1,2-dibromo-4,5-difluorobenzene (Aldrich), 4.2 g (25 mmol) of 4-methylthiophenylboronic acid (Example 1, Step 2), and 3.1 g (22 mmol) of 4-fluorophenylboronic acid in 100 mL of toluene, 100 mL of ethanol, and 100 mL of 2M Na2CO3. After vigorous stirring at reflux overnight, the solvent was removed in vacuo and the residue dissolved in ethyl acetate. The resulting solution was washed with water and dried over MgSO4. Purification by silica gel chromatography gave 1,2-difluoro-4-(4-fluorophenyl)-5-[4-(methylthio)phenyl]benzene as a semi-solid which was used without further purification.

Workup

  1. temperatureat reflux overnight
  2. customthe solvent was removed in vacuo
  3. dissolutionthe residue dissolved in ethyl acetate
  4. washThe resulting solution was washed with water
  5. dry with materialdried over MgSO4
  6. customPurification by silica gel chromatography

Sources & evidence

ORD record
ord-5e8aee7342874cc4a2ac63bb5c51e683
Source dataset
uspto-grants-2004_01
Patent number
US06677488B2

Reaction notes

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