Potassium Carbonate → HCID 12017554, compound

HRID 2303374Notes

Reaction equation

HRID 2303374 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[S:13][C:12]3[CH:14]=[C:15]([O:18][CH3:19])[CH:16]=[CH:17][C:11]=3[C:10]=2[C:20]([C:22]2[CH:27]=[CH:26][C:25]([OH:28])=[CH:24][CH:23]=2)=[O:21])=[CH:5][CH:4]=1.[Br:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37]Br.C([O-])([O-])=O.[K+].[K+]>CC(=O)CC>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([C:9]2[S:13][C:12]3[CH:14]=[C:15]([O:18][CH3:19])[CH:16]=[CH:17][C:11]=3[C:10]=2[C:20]([C:22]2[CH:23]=[CH:24][C:25]([O:28][CH2:37][CH2:36][CH2:35][CH2:34][CH2:33][CH2:32][CH2:31][CH2:30][Br:29])=[CH:26][CH:27]=2)=[O:21])=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 783101,8-DibromooctaneHCID 98651972-(4-Methoxyphenyl)-3-(4-Hydroxybenzoyl)-6-Methoxybenzo[b]thiophene

Product 1

HCID 12017554HCID 12017554, compound

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

750 mg (1.92 mmol) of [2-(4-Methoxyphenyl)-6-methoxybenzo[b]thien-3-yl][4-hydroxyphenyl]methanone, 5.23 g (19.2 mmol) of 1,8-dibromooctane, and 2.66 mg (19.2 mmol) of K2CO3 were combined in 150 mL of 2-butanone. The reaction mixture was stirred and heated to reflux under a nitrogen atmosphere. The reaction was allowed to proceed for three hours, cooled to ambient temperature, and filtered. The solvent was removed by evaporation in vacuo to a yellow oil. The crude product was further purified by chromatography on a silica gel column eluted with a linear gradient begining with hexane and ending with hexane-EtOAc (5:1) (v/v). The desired fractions were determined by tlc, combined, and evaporated to dryness. This yielded 1.28 g (114%; some EtOAc was present in the solid) of the title compound as a yellow, amorphous powder.

Workup

  1. temperatureheated
  2. temperatureto reflux under a nitrogen atmosphere
  3. filtrationfiltered
  4. customThe solvent was removed by evaporation in vacuo to a yellow oil
  5. customThe crude product was further purified by chromatography on a silica gel column
  6. washeluted with a linear gradient
  7. customevaporated to dryness

Sources & evidence

ORD record
ord-413eebb443724a2d8f8915c789851260
Source dataset
uspto-grants-2002_08
Patent number
US06432983B1

Reaction notes

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