Water → 3-[(Carboxyphenyl)sulfanyl]benzenecarboxylic acid

HRID 604961Notes

Reaction equation

I[C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([OH:7])=[O:6].[C:11](=[O:14])([O-])[O-:12].[K+].[K+].[S-2:17].[Na+].[Na+].O>CN(C=O)C.[Cu](I)I>[C:5]([C:4]1[CH:8]=[CH:9][CH:10]=[CH:2][C:3]=1[S:17][C:2]1[CH:10]=[C:9]([C:11]([OH:12])=[O:14])[CH:8]=[CH:4][CH:3]=1)([OH:7])=[O:6]

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of 3-iodobenzoic acid (24.8 g, 100.0 mmol) was dissolved in anhydrous DMF (100.0 mL) was added potassium carbonate (6.9 g, 50.0 mmol). The reaction mixture was heated to 100° C. for 5 minutes and sodium sulphide (4.3 g, 55.0 mmol) and copper iodide (1.9 g, 10.0 mmol) was added and the reaction mixture was heated to reflux under an atmosphere of nitrogen for 12 hours. Water (500.0 mL) was then added and the reaction mixture was heated to boiling with activated carbon. The carbon was filtered off while hot into an excess of 6N HCl (50.0 mL). A precipitate formed on cooling to room temperature and was collected by filtration and washed with water to afford (5.36 g, 19.5%) of the desired 3-[(carboxyphenyl)sulfanyl]benzenecarboxylic acid (GM71/7) as an off-white powder. M.S. m/z 272.73 (M−1)+. 1H NMR (300.13, d6-DMSO) 7.32-7.63 (4H, m, 4×ArH), 7.84-7.99 (4H, m, 4×ArH).

Workup

temperaturethe reaction mixture was heated
temperatureto reflux under an atmosphere of nitrogen for 12 hours
temperaturethe reaction mixture was heated
filtrationThe carbon was filtered off while hot into an excess of 6N HCl (50.0 mL)
customA precipitate formed
temperatureon cooling to room temperature
filtrationwas collected by filtration
washwashed with water

Sources & evidence

ORD record: ord-9ee6d3f05c37480ca18511a320497b1d
Source dataset: uspto-grants-2011_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07910770B2

Reaction notes

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