(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-d9971497620a4066b2c310cd28d13213

Source dataset

uspto-grants-2012_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08314111B2