Diglyme → 1-Bromo-3-butylbenzene

HRID 30556Notes

Reaction equation

HRID 30556 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:8](=O)[CH2:9][CH2:10][CH3:11])[CH:5]=[CH:6][CH:7]=1.COCCOCCOC.NN.[OH-].[K+]>O>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH2:8][CH2:9][CH2:10][CH3:11])[CH:3]=1

Participants

6

Reactant 4

HCID 8150DiglymeHCID 9321HydrazineHCID 14797Potassium HydroxideHCID 184177011-(3-Bromophenyl)butan-1-one

Product 1

HCID 139541021-Bromo-3-butylbenzeneYield 86.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 1-(3-bromophenyl)butan-1-one (1.0 g, 4.4 mmol) and diglyme (10 mL) was treated with hydrazine (1.49 g, 44 mmol), stirred at 100° C. for 2 h, treated with KOH (1.23 g, 22 mmol), stirred at 150° C. for 6 hours, cooled to room temperature, poured into water and extracted with ethyl ether. The organic extracts were combined, dried over MgSO4 and concentrated under vacuum. Purification of the resultant residue on silica gel (ISCO) using hexanes as the eluting solvent gave 1-bromo-3-butylbenzene as a clear oil (0.81 g, 86% yield).

Workup

  1. stirringstirred at 150° C. for 6 hours
  2. temperaturecooled to room temperature
  3. extractionextracted with ethyl ether
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated under vacuum
  6. customPurification of the resultant residue on silica gel (ISCO)

Sources & evidence

ORD record
ord-1a31ab5772f048ecb1712cd3bf9f24b1
Source dataset
uspto-grants-2008_09
Patent number
US07423158B2

Reaction notes

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