Acetic Acid → 8-Bromo-2-methoxy-1-methyl-11,12-dihydro-dibenzo[a,e]cyclooctene-5,6-dione

HRID 730179Notes

Reaction equation

HRID 730179 reaction equation
[Br:1][C:2]1[CH:21]=[CH:20][C:5]2[CH2:6][CH2:7][C:8]3[C:16]([CH3:17])=[C:15]([O:18][CH3:19])[CH:14]=[CH:13][C:9]=3[C:10](=[O:12])[CH2:11][C:4]=2[CH:3]=1.C(O)(=[O:24])C.[Se](=O)=O>ClCCl>[Br:1][C:2]1[CH:21]=[CH:20][C:5]2[CH2:6][CH2:7][C:8]3[C:16]([CH3:17])=[C:15]([O:18][CH3:19])[CH:14]=[CH:13][C:9]=3[C:10](=[O:12])[C:11](=[O:24])[C:4]=2[CH:3]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 24007Selenium DioxideHCID 578344888-Bromo-2-methoxy-1-methyl-11,12-dihydro-6H-dibenzo[a,e]cycloocten-5-one

Product 1

HCID 578344828-Bromo-2-methoxy-1-methyl-11,12-dihydro-dibenzo[a,e]cyclooctene-5,6-dioneYield 68%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of 8-bromo-2-methoxy-1-methyl-11,12-dihydro-6H-dibenzo [a,e]cycloocten-5-one 12 (1.0 g: 2.9 mmol), acetic acid and selenium dioxide (0.64 g; 5.8 mmol) was stirred at 150° C. for 2 hr, cooled to room temperature, diluted with dichloromethane and filtered through silica gel to remove the suspended solids. The filtrate was evaporated to dryness. The residue was heated in ethyl acetate and crystallized by adding hexane to give compound 13 as grey needles, 0.71 g, 68% yield.

Workup

  1. temperaturecooled to room temperature
  2. filtrationfiltered through silica gel
  3. customto remove the suspended solids
  4. customThe filtrate was evaporated to dryness
  5. temperatureThe residue was heated in ethyl acetate
  6. customcrystallized
  7. additionby adding hexane

Sources & evidence

ORD record
ord-91e7649e6aa143faae9cbb4f4cbb25d5
Source dataset
uspto-grants-2009_09
Patent number
US07582667B2

Reaction notes

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