1-Chloro-3,5-dimethoxybenzene → 3-Acetyl-3',5'-dimethoxybiphenyl

HRID 227879

Reaction equation

HRID 227879 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5](Cl)[CH:6]=[C:7]([O:9][CH3:10])[CH:8]=1.[OH-].[OH-].[C:14]([C:17]1[CH:18]=[C:19]([B+2])[CH:20]=[CH:21][CH:22]=1)(=[O:16])[CH3:15].[F-].[K+]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C(P(C(C)(C)C)C1C=CC=CC=1C1C=CC=CC=1)(C)(C)C>[C:14]([C:17]1[CH:22]=[C:21]([C:5]2[CH:4]=[C:3]([O:2][CH3:1])[CH:8]=[C:7]([O:9][CH3:10])[CH:6]=2)[CH:20]=[CH:19][CH:18]=1)(=[O:16])[CH3:15]

Participants

6

Reactant 3

HCID 815021-Chloro-3,5-dimethoxybenzeneHCID 522689Potassium FluorideHCID 178419130HCID 178419130, compound

Product 1

HCID 222184053-Acetyl-3',5'-dimethoxybiphenylYield 91%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 27342152-(Di-tert-butylphosphino)biphenylCatalyst

Procedure

An oven dried Schlenk tube was evacuated and backfilled with argon and charged with palladium acetate (2.2 mg, 0.01 mmol, 1.0 mol %), 2-(di-tert-butylphosphino)biphenyl (6.0 mg, 0.020 mmol, 2.0 mol %), 3,5-dimethoxyphenyl chloride (173 mg, 1.0 mmol), 3-acetylphenylboron dihydroxide (246 mg, 1.5 mmol), and potassium fluoride (174 mg, 3.0 mmol). The tube was evacuated and backfilled with argon, and THF (1 mL) was added through a rubber septum. The reaction mixture was stirred at room temperature until the starting aryl chloride had been completely consumed as judged by GC analysis. The reaction mixture was then diluted with ethyl acetate (30 mL) and poured into a separatory funnel. The mixture was washed with 2.0 M NaOH (20 mL). The organic layer was washed with brine (20 mL), dried over anhydrous magnesium sulfate, filtered, and concentrated. The crude material was purified by flash chromatography on silica gel to afford 232 mg (91%) of the title compound.

Workup

  1. customAn oven dried Schlenk tube
  2. customwas evacuated
  3. customThe tube was evacuated
  4. additionwas added through a rubber septum
  5. customhad been completely consumed
  6. additionThe reaction mixture was then diluted with ethyl acetate (30 mL)
  7. additionpoured into a separatory funnel
  8. washThe mixture was washed with 2.0 M NaOH (20 mL)
  9. washThe organic layer was washed with brine (20 mL)
  10. dry with materialdried over anhydrous magnesium sulfate
  11. filtrationfiltered
  12. concentrationconcentrated
  13. customThe crude material was purified by flash chromatography on silica gel

Sources & evidence

ORD record
ord-78578de76b944a7db4954de3de84ee0a
Source dataset
uspto-grants-2009_07
Patent number
US07560582B2

Linked notes

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