Methanol → 7-Bromo-1,2,3,4-tetrahydronaphthalen-1-one

HRID 1921597Notes

Reaction equation

HRID 1921597 reaction equation
[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][CH2:8][C:9]2=NNC(N)=S)=[CH:4][CH:3]=1.C[OH:18].NNC(N)=S>CC(O)=O>[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][CH2:8][C:9]2=[O:18])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 2723789ThiosemicarbazideHCID 73225505HCID 73225505, compound

Product 1

HCID 2527317-Bromo-1,2,3,4-tetrahydronaphthalen-1-oneYield 68%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

7-Bromo-1-tetralone thiosemicarbazone (21) Into a round bottom flask containing the appropriate ketone (0.347 g, 1.54 mmol), 10 mL of anhydrous methanol were added and the solution was refluxed for about 10 minutes. To the warm ketone solution, thiosemicarbazide (0.246 g, 2.70 mmol) and 0.7 mL of 1% solution of HOAc were added. The reaction mixture was refluxed under nitrogen atmosphere for 18 h, at which point, the solvent was evaporated. The crude reaction mixture was purified by flash chromatography (30% EtOAc/70% hex) which afforded 0.314 g (1.05 mmol) of the product in a 68% yield.

Workup

  1. additionwere added
  2. temperaturethe solution was refluxed for about 10 minutes
  3. temperatureThe reaction mixture was refluxed under nitrogen atmosphere for 18 h, at which point
  4. customthe solvent was evaporated
  5. customThe crude reaction mixture
  6. customwas purified by flash chromatography (30% EtOAc/70% hex) which

Sources & evidence

ORD record
ord-1f3cd1a9ac174dd0810a6217f7119bbe
Source dataset
uspto-grants-2012_05
Patent number
US08173696B2

Reaction notes

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