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Hydrochloric Acid → 2-(4-Bromophenoxy)pyridine

HRID 40698
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HRID 40698 반응식
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.[H-].[Na+].F[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=1.Cl>CN(C=O)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=2)=[CH:4][CH:3]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 78084-BromophenolHCID 97462-FluoropyridineHCID 24758Sodium hydride

생성물 1

HCID 232019352-(4-Bromophenoxy)pyridine수율 77.2%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

4-Bromophenol (2 g, 11.5 mmol) is placed in 10 ml of anhydrous DMF under nitrogen. Sodium hydride (0.51 g, 127 mmol) is added. After stirring for 20 min at ambient temperature, 2-fluoropyridine (1.05 ml, 12.1 mmol) is added and the reaction medium is heated at 105° C. for 7 h. After hydrolysis, the pH is adjusted to 8 with a 1N aqueous solution of HCl. The reaction medium is then extracted with ethyl acetate. The organic phase is washed with a saturated aqueous sodium chloride solution, dried over MgSO4 and concentrated to dryness. The crude product obtained is chromatographed on silica gel, elution being carried out with a gradient of ethyl acetate in heptane ranging from 0% to 30%. 2.22 g of expected 2-(4-bromo-phenoxy)pyridine are obtained,

후처리

  1. temperaturethe reaction medium is heated at 105° C. for 7 h
  2. customAfter hydrolysis
  3. extractionThe reaction medium is then extracted with ethyl acetate
  4. washThe organic phase is washed with a saturated aqueous sodium chloride solution
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated to dryness
  7. customThe crude product obtained
  8. customis chromatographed on silica gel, elution

출처 및 근거

ORD 기록
ord-55b4b911dcaf480b88a1b9de8397e19c
출처 데이터셋
uspto-grants-2013_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08530477B2

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