1-Tetralone → 5-Bromo-1,2,3,4-tetrahydronaphthalen-1-one
Reaction equation
[Al+3].[Cl-].[Cl-].[Cl-].[C:5]1(=[O:15])[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH2:8][CH2:7][CH2:6]1.[Br:16]Br>C([O-])(O)=O.[Na+]>[Br:16][C:10]1[CH:11]=[CH:12][CH:13]=[C:14]2[C:9]=1[CH2:8][CH2:7][CH2:6][C:5]2=[O:15]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 90 °C
Procedure
(Cornelius, L. A. H.; Combs, D. W. Synthetic Communications 1994, 24(19), 2777-2788) Into a round bottom flask kept at 0° C., AlCl3 (19.6 g, 146.8 mmol) was added and the reaction system was put under nitrogen. 8 mL of tetralone (8.62 g, 58.9 mmol) were added during a 10-minute period, at which point, the reaction mixture was heated in an oil bath at 90° C. for about 45 minutes before adding 3.6 mL of Br2 (11.2 g, 70.1 mmol). The reaction mixture was stirred at 90° C. for an hour before 30 mL of ice-water and 20 mL of NaHCO3 were added. The product was extracted twice from the aqueous phase with Et2O and, the resultant organic phase was washed once with NaHCO3, once with brine and dried under Na2SO4. The crude reaction mixture was purified by flash chromatography (2.5% EtOAc/97.5% hex) which afforded 5.87 g (26.1 mmol) of the product in a 44% yield.
Workup
- custom(Cornelius, L. A. H.; Combs, D. W. Synthetic Communications 1994, 24(19), 2777-2788) Into a round bottom flask kept at 0° C.
- additionwere added
- extractionThe product was extracted twice from the aqueous phase with Et2O
- washthe resultant organic phase was washed once with NaHCO3, once with brine
- customdried under Na2SO4
- customThe crude reaction mixture
- customwas purified by flash chromatography (2.5% EtOAc/97.5% hex) which
Sources & evidence
- ORD record
- ord-3ddedf6d20854c8f9196708c169882f2
- Source dataset
- uspto-grants-2012_05
- Patent number
- US08173696B2
Reaction notes
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