Methanol → HCID 118253614, compound

HRID 716601Notes

Reaction equation

HRID 716601 reaction equation
[C:1]1([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1[CH:8]=[CH:9][C:10]2[N:11]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[C:12]3[C:17]([C:18]=2[CH:19]=1)=[CH:16][C:15]([Br:20])=[CH:14][CH:13]=3.CO>ClCCl.[Fe](Cl)(Cl)Cl>[Br:20][C:15]1[CH:14]=[CH:13][C:12]2[N:11]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[C:10]3[CH:9]=[C:8]4[C:32]5[C:27]([C:1]6[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=6[C:7]4=[CH:19][C:18]=3[C:17]=2[CH:16]=1)=[CH:28][CH:29]=[CH:30][CH:31]=5

Participants

5

Reactant 2

HCID 887MethanolHCID 118253613HCID 118253613, compound

Product 1

HCID 118253614HCID 118253614, compoundYield 73.1%

Reagents, catalysts & solvents 2

HCID 24380Iron chloride (FeCl3)CatalystHCID 6344DichloromethaneSolvent

Procedure

In a 3000 ml three-necked flask that had been degassed and filled with nitrogen, 19.9 g (42 mmol) of 3-(biphenyl-2-yl)-6-bromo-9-phenyl-9H-carbazole was dissolved in anhydrous dichloromethane (1000 ml), 68.2 g (420 mmol) Iron(III) chloride was then added, and the mixture was stirred 10 minutes. Methanol 300 ml were added to the mixture and the organic layer was separated and the solvent removed in vacuo. The residue was purified by column chromatography on silica(hexane-dichloromethane) afforded a white solid (14.5 g, 30.7 mmol, 73%).

Workup

  1. customIn a 3000 ml three-necked flask that had been degassed
  2. customthe organic layer was separated
  3. customthe solvent removed in vacuo
  4. customThe residue was purified by column chromatography on silica(hexane-dichloromethane)

Sources & evidence

ORD record
ord-43e71b2da178485db32c3fc7b60584fa
Source dataset
uspto-grants-2015_11
Patent number
US09190619B2

Reaction notes

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