(2-Chlorophenyl)(2,2-diethoxyethyl)sulfane → 7-Chloro-1-benzothiophene

To a solution of 1-chloro-2-(2,2-diethoxyethylsulfanyl)benzene (3.95 g, 15.14 mmol) in toluene (40 mL) was added polyphosphoric acid (15 g, 137.5 mmol). The mixture was heated at reflux for 4 h. then was poured in to ice water, stirred for 30 min and extracted with toluene. The combined toluene extracts were washed with aqueous sodium bicarbonate followed by brine, dried over anhydrous sodium sulfate and evaporated under reduced pressure to yield the crude product. This material was purified by chromatography over silica gel eluting with hexane to afford pure 7-chlorobenzo[b]thiophene (1.72 g, 67.5%). 1H NMR (400 MHz, CDCl3) δ=7.13-7.30 (m, 3H), 7.38 (d, J=5.31 Hz, 1H), 7.62 (dd, J=7.33, 1.52 Hz, 1H); MS (ES+): m/z 169.06 [MH+].

1. temperatureThe mixture was heated
2. temperatureat reflux for 4 h.
3. extractionextracted with toluene
4. washThe combined toluene extracts were washed with aqueous sodium bicarbonate
5. dry with materialdried over anhydrous sodium sulfate
6. customevaporated under reduced pressure
7. customto yield the crude product
8. customThis material was purified by chromatography over silica gel eluting with hexane

ORD record

ord-8340a3bafd4e488682c0b5dc14ea5a7f

Source dataset

uspto-grants-2014_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08796455B2