Methanol → HCID 16122314, compound

HRID 221183Notes

Reaction equation

HRID 221183 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([O:21][CH3:22])[CH:16]=2)[CH:6]=[CH:7][CH:8]=1.CO>ClCCl.[Fe](Cl)(Cl)Cl>[CH3:22][O:21][C:17]1[CH:18]=[CH:19][C:20]2[C:6]3[C:5](=[CH:4][C:3]([O:2][CH3:1])=[CH:8][CH:7]=3)[C:9]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[C:15]=2[CH:16]=1

Participants

5

Reactant 2

HCID 887MethanolHCID 161222203,3′′-Dimethoxy-1,1′:2′,1′′-terphenyl

Product 1

HCID 16122314HCID 16122314, compoundYield 70.5%

Reagents, catalysts & solvents 2

HCID 24380Iron chloride (FeCl3)CatalystHCID 6344DichloromethaneSolvent

Procedure

Into a flask, 2 g of 1,2-bis(3-methoxyphenyl)benzene was put, and allowed to dissolve in 100 ml of dichloromethane under nitrogen atmosphere. In the solution, 3.25 g of iron(III) chloride was added, and the solution was stirred at room temperature for 56.5 hours. Methanol was added to terminate the reaction, and then the solution was washed by water. The organic layer was purified by silica gel column chromatography, and then recrystallized in a toluene/heptane mixed solvent, and thus 1.4 g of 2,7-dimethoxytriphenylene was obtained. Obtained 2,7-dimethoxytriphenylene was converted to 2,7-dihydroxytriphenylene by boron tribromide, and allowed to react with trifluoromethanesulfonyl chloride, and converted to 2,7-bis(trifluoromethanesulfonyloxy)triphenylene. The product was allowed react with bis(pinacolate)diboron, and thus 2,7-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolanyl)triphenylene was synthesized.

Workup

  1. customto terminate
  2. customthe reaction
  3. washthe solution was washed by water
  4. customThe organic layer was purified by silica gel column chromatography
  5. customrecrystallized in a toluene/heptane mixed solvent

Sources & evidence

ORD record
ord-5b78d75bb38548288b051798ac288750
Source dataset
uspto-grants-2012_06
Patent number
US08202633B2

Reaction notes

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