1,3-Dibromopropane → HCID 19389133, compound

HRID 1110286Notes

Reaction equation

HRID 1110286 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([OH:8])[CH:5]=[CH:6][CH:7]=1.[Br:9][CH2:10][CH2:11][CH2:12]Br.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[Br:9][CH2:10][CH2:11][CH2:12][O:8][C:4]1[CH:3]=[C:2]([Br:1])[CH:7]=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 80011,3-DibromopropaneHCID 11430Potassium CarbonateHCID 115633-Bromophenol

Product 1

HCID 19389133HCID 19389133, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 5.0 g (0.029 mol) of 3-bromophenol, 29 ml (0.29 mol) of 1,3-dibromopropane and 12 g (0.087 mol) of potassium carbonate in 75 ml of acetone was stirred at reflux for 22 ours. The reaction mixture was filtered and the filtrate was concentrated at reduced pressure. The residue was purified by HPLC using 3% ethyl acetate-hexane to give 4.9 g (58% yield) of 3-(3-bromopropoxy)bromobenzene. The structure was confirmed by the nmr spectrum.

Workup

  1. temperatureat reflux for 22 ours
  2. filtrationThe reaction mixture was filtered
  3. concentrationthe filtrate was concentrated at reduced pressure
  4. customThe residue was purified by HPLC

Sources & evidence

ORD record
ord-c01d10dd6b914b0898040f4528af829d
Source dataset
uspto-grants-1994_06
Patent number
US05324747

Reaction notes

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