Potassium Carbonate → 2,4-Difluoro-4'-(3-nitro-benzyloxy)-biphenyl

HRID 547846노트

반응식

HRID 547846 반응식
Br[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([N+:9]([O-:11])=[O:10])[CH:4]=1.[F:12][C:13]1[CH:18]=[C:17]([F:19])[CH:16]=[CH:15][C:14]=1[C:20]1[CH:25]=[CH:24][C:23]([OH:26])=[CH:22][CH:21]=1.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[F:12][C:13]1[CH:18]=[C:17]([F:19])[CH:16]=[CH:15][C:14]=1[C:20]1[CH:25]=[CH:24][C:23]([O:26][CH2:2][C:3]2[CH:8]=[CH:7][CH:6]=[C:5]([N+:9]([O-:11])=[O:10])[CH:4]=2)=[CH:22][CH:21]=1

참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 77568Benzene, 1-(bromomethyl)-3-nitro-HCID 1009552',4'-Difluoro(1,1'-biphenyl)-4-ol

생성물 1

HCID 582877952,4-Difluoro-4'-(3-nitro-benzyloxy)-biphenyl수율 63.4%

시약·촉매·용매 1

HCID 180Acetone용매

실험 절차

1-Bromomethyl-3-nitro-benzene (110 mg, 0.508 mmol), 2′,4′-difluoro-biphenyl-4-ol (110 mg, 0.533 mmol), and dried, finely ground potassium carbonate (74 mg, 0.533 mmol) in 10 mL acetone were refluxed under argon for 20 hrs. The reaction mixture was cooled, filtered, concentrated and re-dissolved in ethyl acetate. The ethyl acetate solution was washed with saturated NaHCO3, dried over MgSO4, filtered and evaporated in vacuo. The crude product was purified by flash chromatography with a gradient of 0-20% ethyl acetate in hexanes to yield 0.11 g (63%) of 2,4-difluoro-4′-(3-nitro-benzyloxy)-biphenyl. LC-MS (ES) calculated for C19H13F2NO3, 341.32; found m/z 340.3 [M−H]−.

후처리

  1. temperatureThe reaction mixture was cooled
  2. filtrationfiltered
  3. concentrationconcentrated
  4. dissolutionre-dissolved in ethyl acetate
  5. washThe ethyl acetate solution was washed with saturated NaHCO3
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. customevaporated in vacuo
  9. customThe crude product was purified by flash chromatography with a gradient of 0-20% ethyl acetate in hexanes

출처 및 근거

ORD 기록
ord-e0883477654a42e3a7b7fb805db9e4bc
출처 데이터셋
uspto-grants-2011_05
특허 번호
US07939569B1

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