Methanol → Bis(3-bromophenyl)methanone

HRID 1921595Notes

Reaction equation

HRID 1921595 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:8](=NNC(N)=S)[C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([Br:15])[CH:10]=2)[CH:5]=[CH:6][CH:7]=1.C[OH:22].NNC(N)=S>CC(O)=O>[Br:1][C:2]1[CH:3]=[C:4]([C:8]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([Br:15])[CH:10]=2)=[O:22])[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 2723789ThiosemicarbazideHCID 160614971-(Bis(3-bromophenyl)methylene)thiosemicarbazide

Product 1

HCID 12731928Bis(3-bromophenyl)methanoneYield 18%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Bis(3-bromophenyl) ketone thiosemicarbazone (14) Into a round bottom flask containing the appropriate ketone (1.044 g, 3.07 mmol), 35 mL of anhydrous methanol were added and the solution was refluxed for about 15 minutes. To the warm ketone solution, thiosemicarbazide (0.294 g, 3.23 mmol) and 1% solution of HOAc (1.5 mL) were added. The reaction mixture was refluxed under nitrogen atmosphere for 46 h, at which point, the solvent was evaporated and, the crude reaction mixture was purified by flash chromatography (20% EtOAc/80% hex) to obtain 0.231 g (0.559 mmol) of the product in an 18% yield.

Workup

  1. additionwere added
  2. temperaturethe solution was refluxed for about 15 minutes
  3. temperatureThe reaction mixture was refluxed under nitrogen atmosphere for 46 h, at which point
  4. customthe solvent was evaporated
  5. customthe crude reaction mixture
  6. customwas purified by flash chromatography (20% EtOAc/80% hex)

Sources & evidence

ORD record
ord-2bafa9ee83dc4b2f9e782c9aa00a7a7d
Source dataset
uspto-grants-2012_05
Patent number
US08173696B2

Reaction notes

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