1,3-Dibromopropane → 5-Chloro-3-[4-(3-bromopropoxy)benzoyl]-2-phenylbenzofuran

HRID 268360Notes

Reaction equation

HRID 268360 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][C:8]([C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=3)=[C:7]([C:16](=[O:24])[C:17]3[CH:22]=[CH:21][C:20]([OH:23])=[CH:19][CH:18]=3)[C:6]=2[CH:25]=1.[Br:26][CH2:27][CH2:28][CH2:29]Br.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][C:8]([C:10]3[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=3)=[C:7]([C:16](=[O:24])[C:17]3[CH:22]=[CH:21][C:20]([O:23][CH2:29][CH2:28][CH2:27][Br:26])=[CH:19][CH:18]=3)[C:6]=2[CH:25]=1

Participants

5

Reactant 3

HCID 80011,3-DibromopropaneHCID 11430Potassium CarbonateHCID 214353365-Chloro-3-(4-hydroxybenzoyl)-2-phenylbenzofuran

Product 1

HCID 214353905-Chloro-3-[4-(3-bromopropoxy)benzoyl]-2-phenylbenzofuran

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 3.2 g. (9.2 mmol.) of 5-chloro-3-(4-hydroxybenzoyl)-2-phenylbenzofuran, 3.5 ml. (0.035mol.) of 1,3-dibromopropane and 4.0 g. (0.029 mol.) of potassium carbonate in 100 ml. of acetone is refluxed for 3 hours. After cooling, the reaction mixture is filtered and the filtrate is concentrated to give 5-chloro-3-[4-(3-bromopropoxy)benzoyl]-2-phenylbenzofuran.

Workup

  1. additionA mixture of 3.2 g
  2. temperatureAfter cooling
  3. filtrationthe reaction mixture is filtered
  4. concentrationthe filtrate is concentrated

Sources & evidence

ORD record
ord-db33dc7f1ab64a97a8972b2193b3c737
Source dataset
uspto-grants-1976_03
Patent number
US03947470

Reaction notes

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