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

HRID 549498ノート

反応式

HRID 549498 の反応式
[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

参加物

7

反応物 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 81503BromomethylcyclopropaneHCID 86614876HCID 86614876、化合物

生成物 1

HCID 866148783-Bromo-6-(cyclopropylmethoxy)phenanthrene収率 87%

試薬・触媒・溶媒 2

HCID 4875Potassium Iodide触媒HCID 180Acetone溶媒

実験手順

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 was 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%).

後処理

  1. temperatureat reflux for 3 days
  2. extractionthe reaction mixture extracted with ethyl acetate The organic layer
  3. washwas washed 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)

出典と根拠

ORDレコード
ord-61a4e6dcf62b499583111a8784ac2a2f
出典データセット
uspto-grants-2011_05
特許番号
US07943649B2

反応ノート

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