Dimethylformamide → 2-Bromo-1-(3-methylbut-2-enylthio)benzene

HRID 1278845Notes

Reaction equation

HRID 1278845 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[SH:8].CN(C=O)C.C(=O)([O-])[O-].[K+].[K+].Br[CH2:21][CH:22]=[C:23]([CH3:25])[CH3:24]>O>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8][CH2:21][CH:22]=[C:23]([CH3:25])[CH3:24]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 700922-Butene, 1-bromo-3-methyl-HCID 805982-Bromobenzenethiol

Product 1

HCID 106348752-Bromo-1-(3-methylbut-2-enylthio)benzene

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

19.30 g (102.0 mmol) of 2-bromothiophenol, 160 ml of DMF and 15.50 g (112.0 mmol) of potassium carbonate are introduced into a three-necked flask. 13 ml (112.0 mmol) of 1-bromo-3-methyl-2-butene are added dropwise and the mixture is stirred at room temperature for two hours. The reaction medium is poured into water and extracted with ethyl acetate, and the organic phase is separated out after settling, washed with water, dried over magnesium sulphate and evaporated. 26.00 g (99%) of the expected compound are collected in the form of an orange-coloured oil.

Workup

  1. extractionextracted with ethyl acetate
  2. customthe organic phase is separated out
  3. washwashed with water
  4. dry with materialdried over magnesium sulphate
  5. customevaporated
  6. custom26.00 g (99%) of the expected compound are collected in the form of an orange-coloured oil

Sources & evidence

ORD record
ord-be4c95fecbcc412fa64bbc50a4536844
Source dataset
uspto-grants-2002_09
Patent number
US06444709B1

Reaction notes

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