Bis(2-fluorophenyl)methanol → 2,2'-Difluorobenzophenone

HRID 1452994Notes

Reaction equation

HRID 1452994 reaction equation
[F:1][C:2]1[CH:16]=[CH:15][CH:14]=[CH:13][C:3]=1[CH:4]([OH:12])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[F:11]>[O-2].[Mn+2].C1C=CC=CC=1>[F:1][C:2]1[CH:16]=[CH:15][CH:14]=[CH:13][C:3]=1[C:4]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[F:11])=[O:12]

Participants

4

Reactant 1

HCID 18424663Bis(2-fluorophenyl)methanol

Product 1

HCID 676492,2'-DifluorobenzophenoneYield 82.5%

Reagents, catalysts & solvents 2

HCID 160959Manganese oxideCatalystHCID 241BenzeneSolvent

Procedure

To a mixture of 440.4 mg (2.0 mmol) of 2,2′-bisfluorobenzhydrol and 1.04 g (12.0 mmol) of activated manganese oxide was added 10 ml of benzene. The resultant was refluxed for 2 hours. The reaction mixture was cooled to room temperature, and filtrated with celite. The filtrate was concentrated and purified by column chromatography on silica gel (ethyl acetate:hexane=1:5) to give 360 mg (yield: 82%) of the title compound in the form of a yellow solution.

Workup

  1. temperatureThe resultant was refluxed for 2 hours
  2. filtrationfiltrated with celite
  3. concentrationThe filtrate was concentrated
  4. custompurified by column chromatography on silica gel (ethyl acetate:hexane=1:5)

Sources & evidence

ORD record
ord-293d02bbb75f4110b8382932871f03d7
Source dataset
uspto-grants-2009_01
Patent number
US07473793B2

Reaction notes

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