Sodium Carbonate → HCID 68727306, compound

HRID 1516396Notes

Reaction equation

HRID 1516396 reaction equation
[CH3:1][O:2][C:3](=[O:11])[C:4]1[CH:9]=[CH:8][C:7](I)=[CH:6][CH:5]=1.C(=O)([O-])[O-].[Na+].[Na+].[CH3:18][S:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1B(O)O>CO.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:1][O:2][C:3]([C:4]1[CH:9]=[CH:8][C:7]([C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=2[S:19][CH3:18])=[CH:6][CH:5]=1)=[O:11]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 69273Methyl 4-iodobenzoateHCID 27735432-(Methylthio)benzeneboronic acid

Product 1

HCID 68727306HCID 68727306, compoundYield 814.9%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 887MethanolSolvent

Procedure

To a stirring solution of 4-iodobenzoic acid methyl ester (5 g, 0.0019 mol), sodium carbonate (4.04 g, 0.038 mol) and Palladium acetate (4.2 mg, 0.00019 mol) in methanol (30 mL), was added 2-methylmercapto phenyl boronic acid (3.53 g, 0.02 mol) in one lot at 25-30° C. After reflux of 30 min., reaction mixture was poured in ice cold water (100 mL) and product was extracted in ethyl acetate (250 mL). Column purification (100-200 mesh silica gel, 5% hexane in ethyl acetate) gave 4 g of titled product in 81% yield.

Workup

  1. temperatureAfter reflux of 30 min.
  2. customreaction mixture
  3. extractionproduct was extracted in ethyl acetate (250 mL)
  4. customColumn purification (100-200 mesh silica gel, 5% hexane in ethyl acetate)

Sources & evidence

ORD record
ord-81d2f60bcee549b9b6f7d1ec4a8f6bf3
Source dataset
uspto-grants-2012_07
Patent number
US08227492B2

Reaction notes

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