Water → 3-Bromo-6-(cyclopropylmethoxy)phenanthrene

HRID 2117997노트

반응식

HRID 2117997 반응식
[Br:1][C:2]1[CH:3]=[C:4]2[C:13](=[CH:14][CH:15]=1)[CH:12]=[CH:11][C:10]1[CH:9]=[CH:8][C:7]([OH:16])=[CH:6][C:5]2=1.Br[CH2:18][CH:19]1[CH2:21][CH2:20]1.C(=O)([O-])[O-].[K+].[K+].O>CC(C)=O.[I-].[K+]>[Br:1][C:2]1[CH:15]=[CH:14][C:13]2[CH:12]=[CH:11][C:10]3[C:5]([C:4]=2[CH:3]=1)=[CH:6][C:7]([O:16][CH2:18][CH:19]1[CH2:21][CH2:20]1)=[CH:8][CH:9]=3

참가 물질

7

반응물 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 81503BromomethylcyclopropaneHCID 86614876HCID 86614876, 화합물

생성물 1

HCID 866148783-Bromo-6-(cyclopropylmethoxy)phenanthrene수율 87%

시약·촉매·용매 2

HCID 4875Potassium Iodide촉매HCID 180Acetone용매

실험 절차

A mixture of 6-bromophenanthren-3-ol (0.823 g, 3.02 mmol) from Step 1 above, (bromomethyl)cyclopropane (0.5 mL, 5.4 mmol), potassium carbonate (2.5 g, 18 mmol) and potassium iodide (5 mg) in acetone (50 mL) was heated at reflux for 3 days. Water was then added and the reaction mixture extracted with ethyl acetate The organic layer washed with brine, dried over MgSO4, filtered and concentrated. The crude material was purified by flash chromatography on silica (100% hexanes) to provide 3-bromo-6-(cyclopropylmethoxy)phenanthrene (0.859 g, 87%).

후처리

  1. temperatureat reflux for 3 days
  2. extractionthe reaction mixture extracted with ethyl acetate The organic layer
  3. washwashed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude material was purified by flash chromatography on silica (100% hexanes)

출처 및 근거

ORD 기록
ord-b105fbd6f0ee4133b18ce07ef66abaa5
출처 데이터셋
uspto-grants-2008_10
특허 번호
US07442716B2

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