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Dimethylformamide → 4-(Benzyloxy)-1-bromo-2-fluorobenzene

HRID 707497
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HRID 707497 반응식
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][C:3]=1[F:9].CN(C=O)C.C(=O)([O-])[O-].[K+].[K+].[CH2:21](Br)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>O>[CH2:21]([O:8][C:5]1[CH:6]=[CH:7][C:2]([Br:1])=[C:3]([F:9])[CH:4]=1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 6228DimethylformamideHCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 27791534-Bromo-3-fluorophenol

생성물 1

HCID 222739334-(Benzyloxy)-1-bromo-2-fluorobenzene수율 102.9%

시약·촉매·용매 1

HCID 962Water용매

실험 절차

To a mixed solution of a commercially available product of 4-bromo-3-fluorophenol (15.0 g, 78.5 mmol) and DMF (30 mL) were added potassium carbonate (21.7 g, 157 mmol) and benzyl bromide (10.2 mL, 86.4 mmol) at room temperature, and the resultant mixture was stirred at room temperature for 20 minutes and then at 70° C. for 40 minutes. The reaction mixture was cooled to room temperature, then water was added to the reaction mixture, and the resultant solution was extracted with ethyl acetate. An organic layer was washed with water and then with saturated brine. An organic layer was dried over anhydrous magnesium sulfate and then filtrated. The solvent was evaporated under a reduced pressure, and the resultant residue was purified by silica gel column chromatography (heptane:ethyl acetate=5:1) to give the title compound (22.7 g, yield: quantitative).

후처리

  1. extractionthe resultant solution was extracted with ethyl acetate
  2. washAn organic layer was washed with water
  3. dry with materialAn organic layer was dried over anhydrous magnesium sulfate
  4. filtrationfiltrated
  5. customThe solvent was evaporated under a reduced pressure
  6. customthe resultant residue was purified by silica gel column chromatography (heptane:ethyl acetate=5:1)

출처 및 근거

ORD 기록
ord-d385ff52753b4369a063c5f9e2ad8868
출처 데이터셋
uspto-grants-2015_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09174998B2

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