Triphenylphosphine → 3-Bromo-6-(2-cyclopropylethoxy)phenanthrene

HRID 2118003Notes

Reaction equation

HRID 2118003 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.[CH:17]1([CH2:20][CH2:21]O)[CH2:19][CH2:18]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(OC(/N=N/C(OC(C)(C)C)=O)=O)(C)C>C1COCC1>[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][CH2:21][CH2:20][CH:17]1[CH2:19][CH2:18]1)=[CH:8][CH:9]=3

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 1376422-Cyclopropylethan-1-olHCID 6034084Di-tert-butyl diazene-1,2-dicarboxylateHCID 86614876HCID 86614876, compound

Product 1

HCID 866148853-Bromo-6-(2-cyclopropylethoxy)phenanthrene

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of 6-bromophenanthren-3-ol (3 g, 11 mmol) from Step 1 of Route A of Example 168, 2-cyclopropylethanol (2.85 g, 33 mmol) and triphenylphosphine (5.78 g, 22 mmol) in THF (50 mL) was added di-tert-butylazodicarboxylate (5.08 g, 22 mmol). The reaction mixture was stirred at room temperature overnight, then quenched with water. The aqueous layer was extracted with ethyl acetate. The combined organic layer washed with brine, dried over MgSO4, filtered and concentrated. The material was purified by flash chromatography on silica (100% hexanes) to afford 3-bromo-6-(2-cyclopropylethoxy)phenanthrene.

Workup

  1. customquenched with water
  2. extractionThe aqueous layer was extracted with ethyl acetate
  3. washThe combined organic layer washed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe material was purified by flash chromatography on silica (100% hexanes)

Sources & evidence

ORD record
ord-5f3b759073fc4667b8260dfaef4fe9a0
Source dataset
uspto-grants-2008_10
Patent number
US07442716B2

Reaction notes

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