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

HRID 227879

반응식

HRID 227879 반응식
[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]

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 167845palladium(II) acetate촉매HCID 27342152-(Di-tert-butylphosphino)biphenyl촉매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-78578de76b944a7db4954de3de84ee0a
출처 데이터셋
uspto-grants-2009_07
특허 번호
US07560582B2

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