HCID 89979039, compound → HCID 58383065, compound

HRID 571600Notes

Reaction equation

HRID 571600 reaction equation
I[C:2]1([O:9][CH3:10])[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][CH2:3]1>CC(C)=O.O.[Pd].[Zn]>[CH3:10][O:9][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1[C:3]1[CH:4]=[CH:5][C:6]([CH3:8])=[CH:7][C:2]=1[O:9][CH3:10]

Participants

5

Reactant 1

HCID 89979039HCID 89979039, compound

Product 1

HCID 58383065HCID 58383065, compoundYield 86.7%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 23994ZincCatalystHCID 18366337Propan-2-one--water (1/1)Solvent

Procedure

Bdb was synthesized according to FIG. 15. Briefly, 1-iodo-5-methylanisole (100 mg, 0.4 mmol) was added in to a mixture of 10% Pd on carbon (100 mg) and zinc powder (100 mg, 1.5 mmol) suspended in 5.2 mL of acetone/water (1:1), and the mixture was stirred at room temperature overnight. The solution was extracted with diethyl ether and the ether layer was collected and dried over anhydrous Na2SO4. The ether was removed under reduced pressure and the residue was applied to a flash column chromatography to afford 2,2′-dimethoxy-4,4′-dimethyl biphenyl as a yellow solid (42 mg, 46%). The conversion of 2,2′-dimethoxy-4,4′-dimethyl biphenyl to 4,4′-bis-bromomethyl-2,2′-dimethoxy-biphenyl was accomplished by following a previously reported procedure and resulted in a 31% yield.

Workup

  1. customBdb was synthesized
  2. extractionThe solution was extracted with diethyl ether
  3. customthe ether layer was collected
  4. dry with materialdried over anhydrous Na2SO4
  5. customThe ether was removed under reduced pressure

Sources & evidence

ORD record
ord-5871256ff8d3433fafc4e5a2f45ae2b6
Source dataset
uspto-grants-2015_05
Patent number
US09029332B2

Reaction notes

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