1,3-Dibromopropane → 1-Bromo-3-(3-bromopropoxy)benzene
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]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
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
- temperatureat reflux for 22 ours
- filtrationThe reaction mixture was filtered
- concentrationthe filtrate was concentrated at reduced pressure
- customThe residue was purified by HPLC
Sources & evidence
- ORD record
- ord-c01d10dd6b914b0898040f4528af829d
- Source dataset
- uspto-grants-1994_06
- Patent number
- US05324747
Reaction notes
Loading…