1-Bromoheptane → 1-Bromo-4-(heptylsulfanyl)benzene

HRID 1440175Notes

Reaction equation

HRID 1440175 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([SH:8])=[CH:4][CH:3]=1.[CH2:9](Br)[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH3:15].[OH-].[Na+]>O>[CH2:9]([S:8][C:5]1[CH:6]=[CH:7][C:2]([Br:1])=[CH:3][CH:4]=1)[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH3:15]

Participants

5

Reactant 3

HCID 123691-BromoheptaneHCID 14798Sodium HydroxideHCID 660494-Bromothiophenol

Product 1

HCID 125212451-Bromo-4-(heptylsulfanyl)benzeneYield 85%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

4-Bromothiophenol (15 g, 0.0794 m) was stirred and heated at 80° C. for 18 hours with n-heptylbromide (14.9 g, 0.0833 m) sodium hydroxide (3.3 g, 0.0833 m) and water (15 mls). The mixture was then added to water (50 mls) and extracted with petroleum spirit 400°-60° (3×50 mls). The combined organic phase was dried over magnesium sulphate and evaporated to yield 4-n-heptylthiobromobonzene (19.5 g, 89% GLC, 85% yield).

Workup

  1. extractionextracted with petroleum spirit 400°-60° (3×50 mls)
  2. dry with materialThe combined organic phase was dried over magnesium sulphate
  3. customevaporated
  4. customto yield 4-n-heptylthiobromobonzene (19.5 g, 89% GLC, 85% yield)

Sources & evidence

ORD record
ord-90f208201df14bc297a8ea2669b3cb29
Source dataset
uspto-grants-1996_03
Patent number
US05498366

Reaction notes

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