1,5-Dibromopentane → HCID 131716418, compound

HRID 2106834Notes

Reaction equation

HRID 2106834 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([SH:8])=[CH:4][C:3]=1[CH2:9][CH2:10][CH3:11].[Br:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17]Br.[OH-].[Na+]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C1(C)C=CC=CC=1.O>[Br:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][S:8][C:5]1[CH:6]=[CH:7][C:2]([CH3:1])=[C:3]([CH2:9][CH2:10][CH3:11])[CH:4]=1

Participants

7

Reactant 3

HCID 81001,5-DibromopentaneHCID 14798Sodium HydroxideHCID 23049371HCID 23049371, compound

Product 1

HCID 131716418HCID 131716418, compoundYield 291.1%

Reagents, catalysts & solvents 3

HCID 74236Tetrabutylammonium BromideCatalystHCID 962WaterSolvent2×HCID 1140TolueneSolvent2×

Procedure

A mixture of 36.5 g of 4-methyl-3-n-propylthiophenol, 11.5 g of 1,5-dibromopentane, 80 ml of water, 0.5 g of tetrabutylammonium bromide and 10 ml of toluene was stirred drastically and heated at 80° to 90° C. At this temperature, a solution of 8.6 g of sodium hydroxide and 20 ml of water was added dropwise to the mixture during 1 hour. The reaction was finished by stirring for 2 hours after the dropwise addition. After cooling, the reaction mixture was added with 150 ml of toluene, and separated to layers. A toluene layer was washed with water, and dried over anhydrous sodium sulfate. Then, the residue obtained by distilling off toluene and an excess of 1,5-dibromopentane under reduced pressure, was purified by silica-gel column chromatography (developing solvents: toluene+n-hexane) to give 45.9 g of the intended 1-bromo-5-(4-methyl-3-n-propylthiophenoxy)-n-pentane (yield: 69.3%) as a colorless oil. nD25 1.5569.

Workup

  1. temperatureheated at 80° to 90° C
  2. stirringby stirring for 2 hours
  3. additionafter the dropwise addition
  4. temperatureAfter cooling
  5. customseparated to layers
  6. washA toluene layer was washed with water
  7. dry with materialdried over anhydrous sodium sulfate
  8. customThen, the residue obtained
  9. distillationby distilling off toluene
  10. customan excess of 1,5-dibromopentane under reduced pressure, was purified by silica-gel column chromatography (developing solvents: toluene+n-hexane)

Sources & evidence

ORD record
ord-49fae2d562b04c05b1b4c73baf3c5086
Source dataset
uspto-grants-1990_06
Patent number
US04931474

Reaction notes

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