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

HRID 2373116Notes

Reaction equation

[C:1]([OH:10])(=[O:9])[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[SH:4].I[C:12]1[CH:13]=[C:14]([O:18][CH3:19])[CH:15]=[CH:16][CH:17]=1.C(=O)([O-])[O-].[K+].[K+]>[Cu].CN1CCCC1=O>[CH3:19][O:18][C:14]1[CH:13]=[C:12]([S:4][C:3]2[CH:5]=[CH:6][CH:7]=[CH:8][C:2]=2[C:1]([OH:10])=[O:9])[CH:17]=[CH:16][CH:15]=1

Participants

Conditions

Temperature: 165 °C

Procedure

First, 2-(3-methoxyphenylthio)benzoic acid was prepared. A stirred mixture of thiosalicylic acid (3.57 g, 23 mmol), 3-iodoanisole (5.42 g, 23 mmol), potassium carbonate (7.04 g, 51 mmol), copper powder (0.29 g, 5 mmol), and N-methylpyrrolidinone (75 mL) was deaerated by sparging with nitrogen for 10 min, heated at 165° C. for 2 h, and then cooled to ambient. The reaction mixture was poured onto a mixture of 500 g of ice plus 40 mL of concentrated HCl. The resulting precipitate was collected, washed with water, and dried. The precipitate was dissolved in acetone and filtered through Celite, then concentrated to deposit a crude product. The product was purified by recrystallization from aqueous ethanol. A tan powder was obtained, mass: 4.60 g (76% of theory).

Workup

customby sparging with nitrogen for 10 min
temperaturecooled
additionThe reaction mixture was poured onto a mixture of 500 g of ice plus 40 mL of concentrated HCl
customThe resulting precipitate was collected
washwashed with water
customdried
dissolutionThe precipitate was dissolved in acetone
filtrationfiltered through Celite
concentrationconcentrated
customThe product was purified by recrystallization from aqueous ethanol
customA tan powder was obtained

Sources & evidence

ORD record: ord-0536f15731294b0d91a9b24a06ada3c7
Source dataset: uspto-grants-2008_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07459263B2

Reaction notes

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