Sodium Carbonate → 2′-(Methylthio)[1,1′-biphenyl]-3-carboxylic acid

HRID 399804Notes

Reaction equation

HRID 399804 reaction equation
[CH3:1][S:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1B(O)O.I[C:13]1[CH:14]=[C:15]([CH:19]=[CH:20][CH:21]=1)[C:16]([OH:18])=[O:17].C(=O)([O-])[O-].[Na+].[Na+]>O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:1][S:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:13]1[CH:14]=[C:15]([CH:19]=[CH:20][CH:21]=1)[C:16]([OH:18])=[O:17]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 120603-Iodobenzoic acidHCID 27735432-(Methylthio)benzeneboronic acid

Product 1

HCID 189453382′-(Methylthio)[1,1′-biphenyl]-3-carboxylic acid

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolvent

Procedure

The mixture of 2-methylthiophenyl-dihydroxyborane (1.55 g) and 3-iodobenzoic acid (2.08 g) in water (30 ml) was stirred at room temperature, then sodium carbonate (2.67 g) and palladium(II) acetate (0.019 g) were added thereto. After stirring at 40° C. overnight, the reaction mixture was filtered and was washed with ether (2×20 ml). The aqueous layer was adjusted to pH 2 with 6N-hydrochloric acid. The crystalline was collected, washed with water, and dried to afford 3-(2-methylthiophenyl)benzoic acid.

Workup

  1. stirringAfter stirring at 40° C. overnight
  2. filtrationthe reaction mixture was filtered
  3. washwas washed with ether (2×20 ml)
  4. customThe crystalline was collected
  5. washwashed with water
  6. customdried

Sources & evidence

ORD record
ord-84a4a05efa1d42788bf86d90fa33de56
Source dataset
uspto-grants-1998_10
Patent number
US05824691

Reaction notes

Loading…