Hydrochloric Acid → HCID 66798094, compound

HRID 511059Notes

Reaction equation

HRID 511059 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>C1COCC1.CCCCCC>[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

7

Reactant 4

HCID 313Hydrochloric AcidHCID 21531Triisopropyl borateHCID 11293384Phenanthrene, 9,10-dihydro-2,7-diiodo-HCID 178418339Butyllithium

Product 1

HCID 66798094HCID 66798094, compound

Reagents, catalysts & solvents 2

HCID 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, 16.5 ml of a 15 percent soln. of n-butyllithium in hexane are added at −70° C. After 1 h, the batch is hydrolysed using 2 N hydrochloric acid and warmed to room temperature. The solution is extracted twice with MTB ether, dried over sodium sulfate, the solvent is removed in vacuo, and the resultant crude product 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% hydrogen peroxide, the batch is stirred at 30-40° C. for 30 min with gentle 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 soln. 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-dihydrophenanthren-2-ol as 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. additionAfter addition of 8 ml of 30% hydrogen peroxide
  5. additionare added
  6. customThe aqueous phase is separated off
  7. extractionextracted three times with ethyl acetate
  8. washphases are washed with dil. ammonium iron(II) sulfate soln
  9. dry with materialand dried 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-f7a2f78bd92e4898ae8f7497712abe52
Source dataset
uspto-grants-2015_08
Patent number
US09096795B2

Reaction notes

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