4,4'-Bis(bromomethyl)benzophenone → HCID 19073282, compound

HRID 1955796Notes

Reaction equation

HRID 1955796 reaction equation
Br[CH2:2][C:3]1[CH:18]=[CH:17][C:6]([C:7]([C:9]2[CH:14]=[CH:13][C:12]([CH2:15]Br)=[CH:11][CH:10]=2)=[O:8])=[CH:5][CH:4]=1.[CH3:19][O-:20].[Na+].[CH3:22][OH:23]>>[CH3:19][O:20][CH2:2][C:3]1[CH:18]=[CH:17][C:6]([C:7]([C:9]2[CH:14]=[CH:13][C:12]([CH2:15][O:23][CH3:22])=[CH:11][CH:10]=2)=[O:8])=[CH:5][CH:4]=1

Participants

3

Reactant 2

HCID 23039244,4'-Bis(bromomethyl)benzophenoneHCID 23694274Sodium methanolate methanol

Product 1

HCID 19073282HCID 19073282, compound

Procedure

A solution of 0.46M NaOMe/MeOH (30 mL) containing 4,4'-bis-bromomethylbenzophenone (2.1 g, 5.7 mmol) was refluxed 42 hours. After cooling, the reaction was partitioned between EtOAc and 5% aq. KHSO4. The organic layer was washed with brine, dried over Na2 SO4 and concentrated. The resulting residue was chromatographed on silica gel using 1:4 EtOAc/hexane to elute 1.11 g (70%) of the title compound.

Workup

  1. temperaturewas refluxed 42 hours
  2. temperatureAfter cooling
  3. customthe reaction was partitioned between EtOAc and 5% aq. KHSO4
  4. washThe organic layer was washed with brine
  5. customdried over Na2 SO4
  6. concentrationconcentrated
  7. customThe resulting residue was chromatographed on silica gel using 1:4 EtOAc/hexane
  8. washto elute 1.11 g (70%) of the title compound

Sources & evidence

ORD record
ord-c514ef6ea2f7485ba9c499b509939538
Source dataset
uspto-grants-1998_07
Patent number
US05776983

Reaction notes

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