Potassium Carbonate → HCID 22616173, compound

HRID 842829Notes

Reaction equation

HRID 842829 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8][CH3:9].[C:10]([C:13]1[CH:18]=[CH:17][C:16](B(O)O)=[CH:15][CH:14]=1)([OH:12])=[O:11].[C:22]([O-])([O-])=O.[K+].[K+]>O1CCOCC1.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH3:22][CH2:9][S:8][C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[C:16]1[CH:17]=[CH:18][C:13]([C:10]([OH:12])=[O:11])=[CH:14][CH:15]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 881662-BromothioanisoleHCID 3121834-Carboxyphenylboronic Acid

Product 1

HCID 22616173HCID 22616173, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 312751,4-DioxaneSolvent

Procedure

To a mixture of 2-bromothioanisole (4.8 g, 23.6 mmol), 4-carboxybenzeneboronic acid (3.92 g, 23.6 mmol) and 2M K2CO3 (35.5 mmol, 71 mmol) in dioxane (20 ml) was added dichlorobis(triphenylphosphine)palladium (II) (415 mg, 0.6 mmol) under Ar. It was refluxed for 2 hrs. After the removal of the solvent, the residue was neutralized by 1 N HCl and extracted with dichloromethane. The organic layer was dried over MgSO4 and concentrated in vacuo to give 4-[(2-ethylthio)phenyl]benzoic acid (5.9 g, 100%). ES-MS (M+H)+=245.

Workup

  1. temperatureIt was refluxed for 2 hrs
  2. customAfter the removal of the solvent
  3. extractionextracted with dichloromethane
  4. dry with materialThe organic layer was dried over MgSO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-8ff591ecef064214b6061d6bd9a53b7a
Source dataset
uspto-grants-2002_04
Patent number
US06376515B2

Reaction notes

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