1-Bromo-2-Chloroethane → 2-Chloro-5-(2-chloroethylthio)thiophene

HRID 2186377Notes

Reaction equation

HRID 2186377 reaction equation
[OH-].[Na+].[Cl:3][C:4]1[S:5][C:6]([SH:9])=[CH:7][CH:8]=1.[Cl:10][CH2:11][CH2:12]Br>C(OCC)(=O)C>[Cl:3][C:4]1[S:5][C:6]([S:9][CH2:12][CH2:11][Cl:10])=[CH:7][CH:8]=1

Participants

5

Procedure

28 cm3 of a 5N aqueous sodium hydroxide solution were added, with stirring, to a solution, cooled to a temperature in the region of 5° C., of 17.9 g of 2-chloro-5-thiophenethiol in 30 cm3 of 1-chloro-2-bromoethane, and then the temperature was allowed to return to the region of 20° C., while stirring was continued for 16 hours. The reaction mixture was diluted with 300 cm3 of ethyl acetate and washed with 3 times 150 cm3 of water. The organic solution was dried over sodium sulfate, filtered, and evaporated under reduced pressure (5 kPa) at a temperature in the region of 45° C. 20.6 g of 2-chloro-5-(2-chloroethylthio)thiophene were obtained in the form of an oil with a brown color.

Workup

  1. customto return to the region of 20° C.
  2. stirringwhile stirring
  3. washwashed with 3 times 150 cm3 of water
  4. dry with materialThe organic solution was dried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated under reduced pressure (5 kPa) at a temperature in the region of 45° C

Sources & evidence

ORD record
ord-bf7f28069ecb4f838249ab7f10cf2a63
Source dataset
uspto-grants-2002_06
Patent number
US06403610B1

Reaction notes

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