1,3,5-Trimethoxy-4-iodobenzene → 2,2',4,4',6,6'-Hexamethoxybiphenyl

HRID 919185Notes

Reaction equation

HRID 919185 reaction equation
I[C:2]1[C:7]([O:8][CH3:9])=[CH:6][C:5]([O:10][CH3:11])=[CH:4][C:3]=1[O:12][CH3:13]>[Cu]>[CH3:13][O:12][C:3]1[CH:4]=[C:5]([O:10][CH3:11])[CH:6]=[C:7]([O:8][CH3:9])[C:2]=1[C:2]1[C:7]([O:8][CH3:9])=[CH:6][C:5]([O:10][CH3:11])=[CH:4][C:3]=1[O:12][CH3:13]

Participants

3

Reactant 1

HCID 122540971,3,5-Trimethoxy-4-iodobenzene

Product 1

HCID 52193412,2',4,4',6,6'-HexamethoxybiphenylYield 78%

Reagents, catalysts & solvents 1

HCID 23978CopperCatalyst

Conditions

Temperature
235 °C

Procedure

Compound 6 (7.0 g, 0.024 mol) and copper powder (2.0 g, 0.03 1 mol) were mixed thoroughly and transferred to a heavy wall, pressure vessel. The vessel was placed into a sand-bath at the initial temperature of 120° C. Once the vessel was secured, the temperature of the bath was raised to 235° C. in 15 min and kept at 235° C. for 1 h. The vessel was allowed to cool and the contents removed and powdered. The product was extracted with methanol for 18 h in a soxhlet. The resultant solution was concentrated in vacuo. Purification of the crude reaction mixture via column chromatography (1:5 ethyl acetate/hexane) yielded 7 (3.1 g, 78%) as a white solid.

Workup

  1. customThe vessel was placed into a sand-bath
  2. customtemperature of 120° C
  3. temperatureto cool
  4. customthe contents removed
  5. extractionThe product was extracted with methanol for 18 h in a soxhlet
  6. concentrationThe resultant solution was concentrated in vacuo
  7. customPurification of the crude
  8. customreaction mixture via column chromatography (1:5 ethyl acetate/hexane)

Sources & evidence

ORD record
ord-17feb5d680ca47cd86bd7b1a674c0883
Source dataset
uspto-grants-2016_03
Patent number
US09273021B2

Reaction notes

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