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

HRID 1612012Notes

Reaction equation

HRID 1612012 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 by 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-a31cb090a68845b891e0ad40e2b1fce0
Source dataset
uspto-grants-2006_01
Patent number
US06992094B1

Reaction notes

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