2-Mercaptobenzoic Acid → 2-[(3-Methoxyphenyl)sulfanyl]benzoic acid

HRID 2373112Notes

Reaction equation

HRID 2373112 reaction equation
[C:1]([OH:10])(=[O:9])[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[SH:4].[CH3:11][O:12][C:13]1[CH:14]=[C:15](I)[CH:16]=[CH:17][CH:18]=1.C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>CCOCC.[Cu]I>[CH3:11][O:12][C:13]1[CH:18]=[C:17]([S:4][C:3]2[CH:5]=[CH:6][CH:7]=[CH:8][C:2]=2[C:1]([OH:10])=[O:9])[CH:16]=[CH:15][CH:14]=1

Participants

7

Reactant 4

HCID 54432-Mercaptobenzoic AcidHCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 69839Benzene, 1-iodo-3-methoxy-

Product 1

HCID 131540002-[(3-Methoxyphenyl)sulfanyl]benzoic acidYield 40%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 3283Diethyl EtherSolvent

Procedure

First, 2-[(3-methoxyphenyl)thio]benzoic acid was prepared. A mixture of thiosalicylic acid (1.5 g, 9.7 mmol), 3-methoxyiodobenzene (4.6 g, 19.4 mmol), copper (I) iodide (0.07 g, 0.4 mmol), potassium carbonate (4.0 g, 29.2 mmol), and N,N-dimethylformamide (25 mL) was heated at reflux for 2 h and then cooled to ambient. The reaction mixture was diluted with ether, washed twice with 10% aqueous HCl, and dried (Na2SO4). The solvent is removed at reduced pressure to deposit a brown solid. The product was purified by recrystallization from heptane to provide 1.0 g (40% of theory) of 2-[(3-methoxyphenyl)thio]benzoic acid as a tan solid. 1H NMR (CDCl3): δ 3.80 (s, 3H), 6.90 (d, 1H), 7.00 (d, 1H), 7.25 (m, 5H), 8.11 (d, 1H).

Workup

  1. customFirst, 2-[(3-methoxyphenyl)thio]benzoic acid was prepared
  2. temperaturewas heated
  3. temperatureat reflux for 2 h
  4. temperaturecooled
  5. washwashed twice with 10% aqueous HCl
  6. dry with materialdried (Na2SO4)
  7. customThe solvent is removed at reduced pressure
  8. customThe product was purified by recrystallization from heptane

Sources & evidence

ORD record
ord-b63701f36ce544c08f35518751e28df6
Source dataset
uspto-grants-2008_12
Patent number
US07459263B2

Reaction notes

Loading…