1,4-Dibromobutane → [2-[[2-(4-Bromobutoxy)ethyl]thio]ethyl]benzene

HRID 2108133Notes

Reaction equation

HRID 2108133 reaction equation
[C:1]1([CH2:7][CH2:8][S:9][CH2:10][CH2:11][OH:12])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Br:13][CH2:14][CH2:15][CH2:16][CH2:17]Br.[OH-].[Na+]>O>[Br:13][CH2:14][CH2:15][CH2:16][CH2:17][O:12][CH2:11][CH2:10][S:9][CH2:8][CH2:7][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 80561,4-DibromobutaneHCID 14798Sodium HydroxideHCID 196052-((2-Phenylethyl)thio)ethanol

Product 1

HCID 23045275[2-[[2-(4-Bromobutoxy)ethyl]thio]ethyl]benzeneYield 77%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 2-[(2-phenylethyl)thio]ethanol (1.0 g), 1,4-dibromobutane (3.79 g), TAB (0.6 g) and 50% aqueous sodium hydroxide (12 ml) was stirred at room temperature under nitrogen for 20 h. The mixture was diluted with water (100 ml), extracted with diethyl ether (2×100 ml), dried and evaporated in vacuo to give an oil. Purification by FCC eluting with cyclohexane followed by System B (5:95) gave the title compound (1.34 g) as a colourless oil. T.l.c. (System F 3:1) Rf 0.62.

Workup

  1. extractionextracted with diethyl ether (2×100 ml)
  2. customdried
  3. customevaporated in vacuo
  4. customto give an oil
  5. customPurification by FCC
  6. washeluting with cyclohexane

Sources & evidence

ORD record
ord-1eb4433065d74c5eae5826e3fe7c575c
Source dataset
uspto-grants-1990_06
Patent number
US04937268

Reaction notes

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