2-Mercaptobenzoic Acid → Methyl 2-(2-nitrophenylthio)benzoate

Temperature

80 °C

A solution of 2-mercaptobenzoic acid (6.0 g, 39.0 mmol) in dimethylacetamide (20 mL) was added to a suspension of sodium hydride (60% in oil, 3.1 g, 77.5 mmol) in dimethylacetamide (15 mL). The mixture was stirred for 5 minutes and 1-fluoro-2-nitrobenzene (5.0 g, 35.5 mmol) was added. The reaction mixture was heated at 80° C. for one hour. The mixture was cooled down to room temperature and methyl iodide (7.3 mL, 117.15 mmol) was added. The reaction mixture was stirred at room temperature 16 hours. The mixture was then poor into water and extracted with a mixture of 75% ethyl acetate in hexanes (3 times). The combined organic layers were washed with water and brine, dried over sodium sulfate, filtered and evaporated. The residue was dissolved in a minimum amount of dichloromethane and hexanes was added to precipitate the product. The solid was filtered and dried to afford title compound 408 (7.81 g, 76%) as a yellow solid. MS (m/z): 312.2 (M+H).

1. temperatureThe mixture was cooled down to room temperature
2. stirringThe reaction mixture was stirred at room temperature 16 hours
3. extractionpoor into water and extracted with a mixture of 75% ethyl acetate in hexanes (3 times)
4. washThe combined organic layers were washed with water and brine
5. dry with materialdried over sodium sulfate
6. filtrationfiltered
7. customevaporated
8. dissolutionThe residue was dissolved in a minimum amount of dichloromethane and hexanes
9. additionwas added
10. customto precipitate the product
11. filtrationThe solid was filtered
12. customdried

ORD record

ord-9456936d51834864bee9ae93d982d519

Source dataset

uspto-grants-2013_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08399452B2