Toluene → HCID 68112726, compound

HRID 2106835Notes

Reaction equation

HRID 2106835 reaction equation
[OH-].[Na+].[Br:3][C:4]1[CH:9]=[CH:8][C:7]([SH:10])=[CH:6][CH:5]=1.C1(C)C=CC=CC=1.Br[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][S:24][C:25]1[CH:30]=[CH:29][C:28]([CH3:31])=[C:27]([CH2:32][CH2:33][CH3:34])[CH:26]=1>O.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC>[Br:3][C:4]1[CH:9]=[CH:8][C:7]([S:10][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][S:24][C:25]2[CH:30]=[CH:29][C:28]([CH3:31])=[C:27]([CH2:32][CH2:33][CH3:34])[CH:26]=2)=[CH:6][CH:5]=1

Participants

7

Reactant 4

HCID 1140TolueneHCID 14798Sodium HydroxideHCID 660494-BromothiophenolHCID 131716418HCID 131716418, compound

Product 1

HCID 68112726HCID 68112726, compoundYield 79.6%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 962WaterSolvent2×

Procedure

10 g of sodium hydroxide was dissolved in 20 ml of water, and then added with 2.0 g of 4-bromothiophenol, 0.5 g of tetrabutylammonium bromide, 3 ml of toluene and 3.3 g of 1-bromo-5(4-methyl-3-n-propylthiophenoxy)-n-pentane obtained by ◯1 , followed by drastic stirring at 80° to 90° C. for 4 hours. After cooling, the reaction solution was poured into 100 ml of water, and extracted two times by 150 ml of toluene. The toluene layer was washed with water and saturated solution of common salt, and distilled to remove the solvent. The obtained residue was purified by silica-gel column chromatography (developing solvents: toluene+n-hexane) to give 3.5 g (yield: 79.6%) of the intended 1-(4-bromophenylthio)-5-(4-methyl-3-n-propylthiophenoxy)-n-pentane as a colorless crystal. Furthermore, it was recrystallized by n-hexane to give m.p. 42° to 43° C.

Workup

  1. customobtained by ◯1
  2. temperatureAfter cooling
  3. extractionextracted two times by 150 ml of toluene
  4. washThe toluene layer was washed with water and saturated solution of common salt
  5. distillationdistilled
  6. customto remove the solvent
  7. customThe obtained residue was purified by silica-gel column chromatography (developing solvents: toluene+n-hexane)

Sources & evidence

ORD record
ord-815b9c4171b543ce9d673cd5a1c68018
Source dataset
uspto-grants-1990_06
Patent number
US04931474

Reaction notes

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