Ammonium Chloride → Benzo(b)thiophene-3-ol

Temperature

-78 °C

A solution of methyl 2-(methylthio)benzoate (4.0 g, 22.00 mmol) in THF (60 mL) was added to a solution of freshly prepared LDA (2M in THF, 17.5 mL, 35 mmol) placed at −78° C. The reaction mixture was stirred for 1 hour at −78° C., then overnight at room temperature. The reaction mixture was diluted by addition of a saturated solution of ammonium chloride (50 mL). The aqueous phase was separated and extracted with ethyl acetate (3×70 mL). The combined organic phases were washed with a saturated solution of sodium chloride (40 mL), dried over sodium sulfate, filtered and concentrated to dryness. The residue was purified by chromatography on silica gel using petroleum ether/ethyl acetate (95:5 to 9:1) as eluent. The title product was obtained as a pink solid (1.74 g, 53%).

1. customplaced at −78° C
2. customovernight
3. customat room temperature
4. customThe aqueous phase was separated
5. extractionextracted with ethyl acetate (3×70 mL)
6. washThe combined organic phases were washed with a saturated solution of sodium chloride (40 mL)
7. dry with materialdried over sodium sulfate
8. filtrationfiltered
9. concentrationconcentrated to dryness
10. customThe residue was purified by chromatography on silica gel

ORD record

ord-1603de6765b1480e830b14249159d323

Source dataset

uspto-grants-2016_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09321769B2