Diethyl Ether → ((2-Bromoethyl)thio)benzene

HRID 647092Notes

Reaction equation

HRID 647092 reaction equation
[C:1]1([SH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Br:8][CH2:9][CH2:10]Br.CCOCC>[Na].C(O)C>[C:1]1([S:7][CH2:10][CH2:9][Br:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 3

HCID 3283Diethyl EtherHCID 78391,2-DibromoethaneHCID 7969Thiophenol

Product 1

HCID 78553((2-Bromoethyl)thio)benzene

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 5360545SodiumSolvent

Procedure

33 g of thiophenol were dissolved in a solution of 6.9 g of sodium in 120 ml of ethanol and the solution was added dropwise to 129 ml of 1,2-dibromoethane. The mixture was heated under reflux for 1 hour and cooled and 250 ml of ether were added. The salt which had precipitated out was filtered off. The filtrate was concentrated and the evaporation residue was fractionated. 55.4 g of a colourless oil with a boiling point of 125° to 130° C. under 12 mm Hg were obtained.

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 1 hour
  3. temperaturecooled
  4. customThe salt which had precipitated out
  5. filtrationwas filtered off
  6. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-602778efe5734894a6598224a6a00d13
Source dataset
uspto-grants-1983_10
Patent number
US04407809

Reaction notes

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