Chlorobenzene → 5-Chlorobenzo(b)thiophene

HRID 2206816Notes

Reaction equation

HRID 2206816 reaction equation
C(O[CH:4](OCC)[CH2:5][SH:6])C.[Cl:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>>[Cl:10][C:11]1[CH:16]=[CH:4][C:5]2[S:6][CH:15]=[CH:14][C:13]=2[CH:12]=1

Participants

3

Reactant 2

HCID 7964Chlorobenzene2×HCID 109426222,2-diethoxy-ethanethiol

Product 1

HCID 113097545-Chlorobenzo(b)thiopheneYield 90%

Procedure

In a 250 mL 2-neck round flask, 4-chlorophenyl) (2,2-diethoxyethyl)sulfane (5 g, 19 mmol) and chlorobenzene (4 mL) were poured, and then the reaction mixture was added to a polyacrylic acid (PAA) reaction solution (5 g) obtained after boiling in chlorobenzen (5 mL). After the reaction, ice water (25 mL) was added to the mixture, and the mixture was washed with brine (50 mL) and dried over Na2SO4. The mixture was subjected to column chromatography using petroleum ether to give 2.9 g of white solid (90% yield).

Workup

  1. customobtained
  2. additionwas added to the mixture
  3. washthe mixture was washed with brine (50 mL)
  4. dry with materialdried over Na2SO4

Sources & evidence

ORD record
ord-13fd8d98dbad4df387826b6725ee6adc
Source dataset
uspto-grants-2016_06
Patent number
US09373794B2

Reaction notes

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