1,5-Dibromopentane → 1-[2-[(5-Bromopentyl)oxy]ethyl]-4-(methylthio)benzene

HRID 568880Notes

Reaction equation

HRID 568880 reaction equation
[CH3:1][S:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][OH:11])=[CH:5][CH:4]=1.[Br:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17]Br.[OH-].[Na+]>O>[Br:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][O:11][CH2:10][CH2:9][C:6]1[CH:7]=[CH:8][C:3]([S:2][CH3:1])=[CH:4][CH:5]=1

Participants

5

Reactant 3

HCID 81001,5-DibromopentaneHCID 14798Sodium HydroxideHCID 27600862-(4-Methylsulfanylphenyl)ethanol

Product 1

HCID 200713861-[2-[(5-Bromopentyl)oxy]ethyl]-4-(methylthio)benzeneYield 76.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

4-(methylthio)benzeneethanol (7.44 g) and 1,5 dibromopentane (30.48 g) were stirred rapidly at room temperature with TAB (1.0 g) and 12.5M aqueous sodium hydroxide (35 ml) for 64 h. The mixture was diluted with water (170 ml), extracted with ER (3×200 ml), and the combined organic extracts were washed consecutively with water (170 ml) and brine (170 ml), dried and evaporated. The residual oil (29.29 g) was purified by FCC eluting with ER-CX (0:100→3:97) to give the title compound as a colourless oil (10.68 g). T.l.c. (ER-CX 1:79) Rf 0.08.

Workup

  1. extractionextracted with ER (3×200 ml)
  2. washthe combined organic extracts were washed consecutively with water (170 ml) and brine (170 ml)
  3. customdried
  4. customevaporated
  5. customThe residual oil (29.29 g) was purified by FCC
  6. washeluting with ER-CX (0:100→3:97)

Sources & evidence

ORD record
ord-e53995d0ce6f4a9f8753765b5e6ed48c
Source dataset
uspto-grants-1988_03
Patent number
US04730008

Reaction notes

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