4,4'-Dichlorobenzophenone → 2-amino-1,1-bis(4-chlorophenyl)ethanol

HRID 1882541Notes

Reaction equation

HRID 1882541 reaction equation
[Cl:1][C:2]1[CH:16]=[CH:15][C:5]([C:6]([C:8]2[CH:13]=[CH:12][C:11]([Cl:14])=[CH:10][CH:9]=2)=[O:7])=[CH:4][CH:3]=1.C[Si]([C:21]#[N:22])(C)C>C(Cl)Cl.[I-].[Zn+2].[I-]>[NH2:22][CH2:21][C:6]([C:8]1[CH:13]=[CH:12][C:11]([Cl:14])=[CH:10][CH:9]=1)([C:5]1[CH:15]=[CH:16][C:2]([Cl:1])=[CH:3][CH:4]=1)[OH:7]

Participants

5

Reactant 2

HCID 70344,4'-DichlorobenzophenoneHCID 82115Trimethylsilyl cyanide

Product 1

HCID 6860732-amino-1,1-bis(4-chlorophenyl)ethanol

Reagents, catalysts & solvents 2

HCID 9883512zinc(II)iodideCatalystHCID 6344DichloromethaneSolvent

Procedure

The title compound is prepared by combining 4,4′-dichlorobenzophenone (5 g, 20 mmol) and zinc iodide (480 mg, 1.49 mmol) in DCM (100 mL). Trimethylsilyl cyanide (2.17 g, 21.9 mmol) is added, and the reaction is stirred at room temperature for 18 hours. The reaction is washed with water (100 mL) and dried over magnesium sulfate, before filtering and removal of the solvent under reduced pressure. The residue is redissolved in dry THF (40 mL), 1.0M borane in THF (40 mL) is added, and the reaction is stirred at reflux for 24 hours. After cooling, the volatile components are removed under reduced pressure, the residue is taken up in methanol (100 mL). Concentrated hydrochloric acid is added, and the reaction is refluxed for a further 2 hours, before once more removing the volatile components under reduced pressure, to give the title compound as a hydrochloride salt.

Workup

  1. customThe title compound is prepared
  2. washThe reaction is washed with water (100 mL)
  3. dry with materialdried over magnesium sulfate
  4. filtrationbefore filtering
  5. customremoval of the solvent under reduced pressure
  6. dissolutionThe residue is redissolved in dry THF (40 mL)
  7. addition1.0M borane in THF (40 mL) is added
  8. stirringthe reaction is stirred
  9. temperatureat reflux for 24 hours
  10. temperatureAfter cooling
  11. customthe volatile components are removed under reduced pressure
  12. additionConcentrated hydrochloric acid is added
  13. temperaturethe reaction is refluxed for a further 2 hours
  14. custombefore once more removing the volatile components under reduced pressure

Sources & evidence

ORD record
ord-79f971da7c124ea19c0c412f04c9022d
Source dataset
uspto-grants-2012_11
Patent number
US08318750B2

Reaction notes

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