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

HRID 268344Notes

Reaction equation

HRID 268344 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-3009629864f94dbebb49dba8c24b09bf
Source dataset
uspto-grants-1976_03
Patent number
US03947470

Reaction notes

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