Potassium Carbonate → 4-(2-Methylthiophenyl)benzoic acid

HRID 2244218Notes

Reaction equation

HRID 2244218 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(=O)([O-])[O-].[K+].[K+]>O.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>[CH3:9][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

7

Reactant 3

HCID 11430Potassium CarbonateHCID 881662-BromothioanisoleHCID 3121834-Carboxyphenylboronic Acid

Product 1

HCID 225963254-(2-Methylthiophenyl)benzoic acid

Reagents, catalysts & solvents 3

HCID 178418476HCID 178418476, compoundCatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

A stirred mixture containing 4.15 g (0.025 mole) of 2-bromothioanisole, 5.08 g. (0.0025 mole) of 4-carboxybenzeneboronic acid, 10.36 g (0.075 mol) of potassium carbonate and 0.45 g (0.00063 mol) of dichlorobis(triphenylphosphine)palladium(II) in 40 mL of water and 20 mL of 1,4-dioxane was heated under reflux for two hours under nitrogen. The reacton mixture was allowed to cool to room temperature and filtered. The dioxane was removed in vacuo, the residue was diluted with 100 mL of water and then acidified with 20% hydrochloric acid. The crude product (6.1 g) was recrystallized from ethanol to yield the title compound, m.p. 220-222° C.

Workup

  1. temperatureunder reflux for two hours under nitrogen
  2. filtrationfiltered
  3. customThe dioxane was removed in vacuo
  4. additionthe residue was diluted with 100 mL of water
  5. customThe crude product (6.1 g) was recrystallized from ethanol

Sources & evidence

ORD record
ord-f3103dfe539e4d11a4cc2b0430f07909
Source dataset
uspto-grants-2010_03
Patent number
US07678787B2

Reaction notes

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