Hydrochloric Acid → HCID 66798094, compound

HRID 1429282Notes

Reaction equation

HRID 1429282 reaction equation
[I:1][C:2]1[CH:15]=[CH:14][C:13]2[C:12]3[C:7](=[CH:8][C:9](I)=[CH:10][CH:11]=3)[CH2:6][CH2:5][C:4]=2[CH:3]=1.B(OC(C)C)(OC(C)C)[O:18]C(C)C.C([Li])CCC.Cl.[OH-].[Na+].OO>C1COCC1.CCCCCC.C1(C)C=CC=CC=1.O>[I:1][C:2]1[CH:3]=[C:4]2[C:13]([C:12]3[CH:11]=[CH:10][C:9]([OH:18])=[CH:8][C:7]=3[CH2:6][CH2:5]2)=[CH:14][CH:15]=1

Participants

11

Reactant 6

HCID 313Hydrochloric Acid2×HCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 21531Triisopropyl borateHCID 11293384Phenanthrene, 9,10-dihydro-2,7-diiodo-HCID 178418339Butyllithium

Product 1

HCID 66798094HCID 66798094, compound

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 1140TolueneSolventHCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Procedure

8.8 g (20.4 mmol) of 2,7-diiodo-9,10-dihydrophenanthrene are dissolved in 250 ml of THF, and, after addition of 7.0 ml (30.5 mmol) of triisopropyl borate at −70° C., 16.5 ml of a 15 percent solution of n-butyllithium in hexane are added. After 1 h, the batch is hydrolysed using 2 N hydrochloric acid and warmed to room temp. The solution is extracted twice with MTB ether, dried over sodium sulfate, the solvent is removed in vacuo, and the crude product obtained is suspended in 80 ml of toluene and 30 ml of 2 N sodium hydroxide solution with vigorous stirring. After addition of 8 ml of 30 percent hydrogen peroxide, the batch is stirred at 30-40° C. for 30 min with cooling, 200 ml of water are added, and the mixture is acidified using 2 N hydrochloric acid. The aqueous phase is separated off and extracted three times with ethyl acetate. The combined org. phases are washed with dil. ammonium iron(II) sulfate solution and dried over sodium sulfate. The solvent is removed in vacuo, and the residue is filtered through silica gel with dichloromethane, giving 7-iodo-9,10-dihydro-phenanthren-2-ol as a colourless solid.

Workup

  1. extractionThe solution is extracted twice with MTB ether
  2. dry with materialdried over sodium sulfate
  3. customthe solvent is removed in vacuo
  4. customthe crude product obtained
  5. temperaturewith cooling
  6. customThe aqueous phase is separated off
  7. extractionextracted three times with ethyl acetate
  8. washphases are washed with dil. ammonium iron(II) sulfate solution
  9. dry with materialdried over sodium sulfate
  10. customThe solvent is removed in vacuo
  11. filtrationthe residue is filtered through silica gel with dichloromethane

Sources & evidence

ORD record
ord-151c1886e1d640648562bf0994fc7965
Source dataset
uspto-grants-2015_01
Patent number
US08940184B2

Reaction notes

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