Dimethylformamide → m-Bromophenyl 3-methyl-2-butenyl sulfide

HRID 858269Notes

Reaction equation

HRID 858269 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([SH:8])[CH:5]=[CH:6][CH:7]=1.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]=[C:4]([S:8][CH2:21][CH:22]=[C:23]([CH3:25])[CH3:24])[CH:3]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 700922-Butene, 1-bromo-3-methyl-HCID 80597m-Bromobenzenethiol

Product 1

HCID 22640690m-Bromophenyl 3-methyl-2-butenyl sulfide

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

25.00 g (132.0 mmol) of 3-bromothiophenol, 200 ml of DMF and 18.23 g (138.0 mmol) of potassium carbonate are introduced into a three-necked flask. 18.0 ml (157.0 mmol) of 1-bromo-3-methyl-2-butene are added dropwise and the mixture is stirred at room temperature for five hours. The reaction medium is poured into water and extracted with ethyl acetate, and the organic phase is separated out after settling has taken place, washed with water, dried over magnesium sulphate and evaporated. 33.00 g (97%) of the expected compound are collected in the form of a yellow oil.

Workup

  1. extractionextracted with ethyl acetate
  2. customthe organic phase is separated out after settling
  3. washwashed with water
  4. dry with materialdried over magnesium sulphate
  5. customevaporated
  6. custom33.00 g (97%) of the expected compound are collected in the form of a yellow oil

Sources & evidence

ORD record
ord-0431190da25d4435a220758f831c06ff
Source dataset
uspto-grants-2006_12
Patent number
US07148245B2

Reaction notes

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