Methanol → 3-Bromobenzophenone

HRID 1921594Notes

Reaction equation

HRID 1921594 reaction equation
[C:1]1([C:7](=NNC(N)=S)[C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([Br:14])[CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C[OH:21].NNC(N)=S>CC(O)=O>[C:1]1([C:7]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([Br:14])[CH:9]=2)=[O:21])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 2723789ThiosemicarbazideHCID 74411416HCID 74411416, compound

Product 1

HCID 705483-BromobenzophenoneYield 34%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Phenyl(3-bromophenyl) ketone thiosemicarbazone (13) Into a round bottom flask containing the appropriate ketone (1.79 g, 6.84 mmol), 30 mL of anhydrous methanol were added and the solution was refluxed for about 15 minutes. To the warm ketone solution, thiosemicarbazide (0.600 g, 6.59 mmol) and 1% solution of HOAc (0.8 mL) were added. The reaction mixture was refluxed under nitrogen atmosphere for 26 h, at which point, the solvent was evaporated and, the crude reaction mixture was purified by flash chromatography (30% EtOAc/70% hex) to obtain 0.7739 g (2.32 mmol) of the product in a 34% yield.

Workup

  1. additionwere added
  2. temperaturethe solution was refluxed for about 15 minutes
  3. temperatureThe reaction mixture was refluxed under nitrogen atmosphere for 26 h, at which point
  4. customthe solvent was evaporated
  5. customthe crude reaction mixture
  6. customwas purified by flash chromatography (30% EtOAc/70% hex)

Sources & evidence

ORD record
ord-d0b1bba57aa94ac0bcf89b0adda14a0b
Source dataset
uspto-grants-2012_05
Patent number
US08173696B2

Reaction notes

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