1-Bromo-3-chloropropane → HCID 131716417, compound

HRID 2106833Notes

Reaction equation

HRID 2106833 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[CH2:13][CH2:14][CH2:15][Cl:16].[OH-].[Na+]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.O>[Cl:16][CH2:15][CH2:14][CH2:13][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

6

Reactant 3

HCID 80061-Bromo-3-chloropropaneHCID 14798Sodium HydroxideHCID 23049371HCID 23049371, compound

Product 1

HCID 131716417HCID 131716417, compoundYield 77.3%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 962WaterSolvent

Procedure

36.4 g of 4-methyl-3-n-propylthio-phenol, 35 g of 3-bromo-1-chloro-n-propane and 3 g of tetrabutylammonium bromide were added into 10% aqueous solution of sodium hydroxide, and this mixture was stirred drastically for 2 hours at room temperature, then for 6 hours at 50° C. After the reaction was finished, the mixture was poured into 200 ml of water, and extracted 2 times by 200 ml of toluene. After the toluene layer was washed with water, toluene was distilled off, and the residue thus obtained was purified by silica-gel column chromatography (developing solvent: toluene+n-hexane) to give 40 g of the intended 1-chloro-3-(4-methyl-3-n-propylthiophenoxy)-n-propane (yield: 77.3%) as a colorless oil, nD25 1.5505.

Workup

  1. waitfor 6 hours at 50° C
  2. extractionextracted 2 times by 200 ml of toluene
  3. washAfter the toluene layer was washed with water, toluene
  4. distillationwas distilled off
  5. customthe residue thus obtained
  6. customwas purified by silica-gel column chromatography (developing solvent: toluene+n-hexane)

Sources & evidence

ORD record
ord-43320ece20784186b6528e98664e190b
Source dataset
uspto-grants-1990_06
Patent number
US04931474

Reaction notes

Loading…