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

HRID 2117997Notes

Reaction equation

HRID 2117997 reaction equation
[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

Participants

7

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 4875Potassium IodideCatalystHCID 180AcetoneSolvent

Procedure

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%).

Workup

  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)

Sources & evidence

ORD record
ord-b105fbd6f0ee4133b18ce07ef66abaa5
Source dataset
uspto-grants-2008_10
Patent number
US07442716B2

Reaction notes

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