1,4-Dibromobutane → HCID 23296311, compound

HRID 1954185Notes

Reaction equation

HRID 1954185 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]2[CH:25]=[CH:24][CH:23]=[C:22](O)[CH:21]=2)=[CH:5][CH:4]=1.[Br:27][CH2:28][CH2:29][CH2:30][CH2:31]Br.C([O-])([O-])=O.[K+].[K+]>CC(=O)CC>[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]2[CH:25]=[CH:24][CH:23]=[C:22]([CH2:31][CH2:30][CH2:29][CH2:28][Br:27])[CH:21]=2)=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 80561,4-DibromobutaneHCID 11430Potassium CarbonateHCID 154853032-(4-Methoxyphenyl)-3-(3-hydroxyphenyl)-6-methoxybenzo[b]thiophene

Product 1

HCID 23296311HCID 23296311, compound

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

A slurry of 4.04 g (11 mmol) of 2-(4-Methoxyphenyl)-3-(3-hydroxyphenyl)-6-methoxybenzo[b]thiophene, 1,4-dibromobutane 26.3 mL (220 mmol), and 3.5 g (25.3 mmol) of K2CO3 in 200 mL of 2-butanone was preapared. The reaction mixture was heated to reflux for two hours, then filtered, and evaporated to dryness. The resulting oil was chromatographed on a silica gel column eluted with a linear gradient begining with EtOAc-hexane (1:9) (v/v) and ending with EtOAc-hexane (1:4) (v/v). The desired fractions were combined and evaporated to a yellow oil. This yielded 5 g of the title compound.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for two hours
  3. filtrationfiltered
  4. customevaporated to dryness
  5. customThe resulting oil was chromatographed on a silica gel column
  6. washeluted with a linear gradient
  7. customevaporated to a yellow oil

Sources & evidence

ORD record
ord-a86c5578632c4cbba4aac15806ba7bbf
Source dataset
uspto-grants-2000_09
Patent number
US06121293

Reaction notes

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