Butyl bromide → Thiophene, 2-(butylthio)-

HRID 1901395Notes

Reaction equation

HRID 1901395 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH3:5].[S:6]1[CH:10]=[CH:9][CH:8]=[C:7]1[SH:11].[Br-].[Na+]>[O-]CC.[Na+]>[CH2:2]([S:11][C:7]1[S:6][CH:10]=[CH:9][CH:8]=1)[CH2:3][CH2:4][CH3:5]

Participants

5

Reactant 3

HCID 8002Butyl bromideHCID 253881Sodium BromideHCID 5226742-Thiophenethiol

Product 1

HCID 520967Thiophene, 2-(butylthio)-

Reagents, catalysts & solvents 1

HCID 2723922Sodium ethoxideSolvent

Conditions

Temperature
80 °C

Procedure

1-Bromobutane (32.76 g, 0.239 mol) was added dropwise to a stirred solution of compound 5 (13.87 g, 0.120 mol) in sodium ethoxide (2.75 g of sodium metal in 100 ml of super-dry ethanol) at room temperature. The solution was heated at 80° C. for 2 h (glc and tlc analysis revealed a complete reaction) and the sodium bromide was filtered off. The solvent was removed in vacuo and the residue was distilled to give a colourless liquid.

Workup

  1. filtrationwas filtered off
  2. customThe solvent was removed in vacuo
  3. distillationthe residue was distilled
  4. customto give a colourless liquid

Sources & evidence

ORD record
ord-97a57743df414a64ac047700d3c2fb13
Source dataset
uspto-grants-1996_11
Patent number
US05578242

Reaction notes

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