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Potassium Carbonate → 1-Bromo-4-(difluoromethoxy)-2-fluorobenzene

HRID 84247
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HRID 84247 반응식
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][C:3]=1[F:9].C(=O)([O-])[O-].[K+].[K+].Cl[C:17]([F:27])([F:26])C(C1C=CC=CC=1)=O>C(#N)C.O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH:17]([F:27])[F:26])=[CH:4][C:3]=1[F:9]
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참가 물질

6

반응물 3

HCID 11430Potassium CarbonateHCID 2382962-Chloro-2,2-difluoroacetophenoneHCID 27791534-Bromo-3-fluorophenol

생성물 1

HCID 652032131-Bromo-4-(difluoromethoxy)-2-fluorobenzene수율 78.3%

시약·촉매·용매 2

HCID 962Water용매HCID 6342Acetonitrile
용매

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온도
80 °C

실험 절차

To a solution of 4-bromo-3-fluoro-phenol (962 mg, 5.037 mmol) in acetonitrile (25 mL) was added a solution of potassium carbonate (28.3 g, 181 mmol) dissolved in water (25 mL) all under nitrogen. To the reaction mixture was added 2-chloro-2,2-difluoroacetophenone (5 g, 25 mmol) and the reaction was heated to 80° C. for 4 hours. The reaction was cooled to room temperature and extracted with ethyl acetate (3×50 mL). The organic layer was dried with sodium sulfate, filtered and concentrated onto silica gel. Silica gel chromotography (5% ethyl acetate 95% heptane to 100% ethyl acetate over 55 minutes) furnished a clear oil (950 mg, 78%). LCMS m/z 531.7 (M−1) 1H NMR (400 MHz, METHANOL-d4) δ ppm 6.85 (s, 1 H) 6.92 (dd, J=8.88, 2.63 Hz, 1 H) 7.05 (t, 1 H) 7.38 (t, 1 H)

후처리

  1. temperatureThe reaction was cooled to room temperature
  2. extractionextracted with ethyl acetate (3×50 mL)
  3. dry with materialThe organic layer was dried with sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated onto silica gel

출처 및 근거

ORD 기록
ord-109cbb36e8154670b55a70f0336a85a5
출처 데이터셋
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08846933B2

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