1,4-Dibromobutane → 3-[4-(4-Bromobutoxy)benzoyl]-2-phenylbenzofuran

HRID 2398444Notes

Reaction equation

HRID 2398444 reaction equation
[OH:1][C:2]1[CH:24]=[CH:23][C:5]([C:6]([C:8]2[C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=3[O:10][C:9]=2[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[O:7])=[CH:4][CH:3]=1.[Br:25][CH2:26][CH2:27][CH2:28][CH2:29]Br.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[Br:25][CH2:26][CH2:27][CH2:28][CH2:29][O:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([C:8]2[C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=3[O:10][C:9]=2[C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)=[O:7])=[CH:23][CH:24]=1

Participants

5

Reactant 3

HCID 80561,4-DibromobutaneHCID 11430Potassium CarbonateHCID 13264991(4-Hydroxyphenyl)(2-phenyl-1-benzofuran-3-yl)methanone

Product 1

HCID 214352643-[4-(4-Bromobutoxy)benzoyl]-2-phenylbenzofuran

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 3.0 g. (9.5 mmol.) of 3-(4-hydroxybenzoyl)-2-phenylbenzofuran, 6.2 g. (0.029 mol.) of 1,4-dibromobutane and 3.9 g. (0.029 mol.) of potassium carbonate in 100 ml. of dry acetone is refluxed for 18 hours. The reaction mixture is cooled, filtered and the filtrate is concentrated under reduced pressure then heated on a steam bath in vacuo to remove excess 1,4-dibromobutane and leave 3-[4-(4-bromobutoxy)benzoyl]-2-phenylbenzofuran as a residue.

Workup

  1. additionA mixture of 3.0 g
  2. temperatureThe reaction mixture is cooled
  3. filtrationfiltered
  4. concentrationthe filtrate is concentrated under reduced pressure
  5. temperaturethen heated on a steam bath in vacuo
  6. customto remove excess 1,4-dibromobutane

Sources & evidence

ORD record
ord-1b3c2f8de0f24bd09ec6b96da03cf334
Source dataset
uspto-grants-1977_05
Patent number
US04024273

Reaction notes

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