Methanol → 6,14-Dimethoxyditriphenyieno[2,3-b:2',3'-d]thiophene

HRID 1753709Notes

Reaction equation

HRID 1753709 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([C:15]2[CH:16]=[CH:17][C:18]3[C:22]4[CH:23]=[CH:24][C:25]([C:27]5[CH:32]=[CH:31][C:30]([O:33][CH3:34])=[CH:29][C:28]=5[C:35]5[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=5)=[CH:26][C:21]=4[S:20][C:19]=3[CH:41]=2)=[C:7]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:8]=1.CO>ClCCl.[Fe](Cl)(Cl)Cl>[CH3:34][O:33][C:30]1[CH:29]=[C:28]2[C:27](=[CH:32][CH:31]=1)[C:25]1[C:24](=[CH:23][C:22]3[C:18]4[CH:17]=[C:16]5[C:15](=[CH:41][C:19]=4[S:20][C:21]=3[CH:26]=1)[C:6]1[C:7](=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=1)[C:9]1[C:14]5=[CH:13][CH:12]=[CH:11][CH:10]=1)[C:40]1[C:35]2=[CH:36][CH:37]=[CH:38][CH:39]=1

Participants

5

Reactant 2

HCID 887MethanolHCID 867300063,7-Bis(5-methoxybiphenyl-2-yl)dibenzo[b,d]thiophene

Product 1

HCID 867300076,14-Dimethoxyditriphenyieno[2,3-b:2',3'-d]thiopheneYield 93%

Reagents, catalysts & solvents 2

HCID 24380Iron chloride (FeCl3)CatalystHCID 6344DichloromethaneSolvent

Procedure

In a 1000 ml three-necked flask that had been deaerated and filled with nitrogen, 4.4 g (8.1 mmol) of 3,7-bis(5-methoxybiphenyl-2-yl)dibenzo[b,d]thiophene was dissolved in anhydrous dichloromethane (400 ml), 13.2 g (81 mmol) iron(III)chloride was then added, and the mixture was stirred one hour. Methanol 200 ml were added to the mixture and the organic layer was separated and the solvent removed in vacuum. The residue was purified by column chromatography on silica(hexane-dichloromethane) afforded a white solid (4.1 g, 7.5 mmol, 93%).

Workup

  1. customIn a 1000 ml three-necked flask that had been deaerated
  2. customthe organic layer was separated
  3. customthe solvent removed in vacuum
  4. customThe residue was purified by column chromatography on silica(hexane-dichloromethane)

Sources & evidence

ORD record
ord-e8281c5c22e2435fa442e7188ffd4ff1
Source dataset
uspto-grants-2015_10
Patent number
US09166177B2

Reaction notes

Loading…