4-bromo-6,7-dimethoxy-1-indanone → HCID 19042284, compound

HRID 2210938Notes

Reaction equation

HRID 2210938 reaction equation
Br[C:2]1[CH:10]=[C:9]([O:11][CH3:12])[C:8]([O:13][CH3:14])=[C:7]2[C:3]=1[CH2:4][CH2:5][C:6]2=[O:15].[Cu][C:17]#[N:18]>CN(C=O)C.O.Cl.C1(C)C=CC=CC=1.O.O.O.O.O.O.[Fe](Cl)(Cl)Cl>[C:17]([C:2]1[CH:10]=[C:9]([O:11][CH3:12])[C:8]([O:13][CH3:14])=[C:7]2[C:3]=1[CH2:4][CH2:5][C:6]2=[O:15])#[N:18]

Participants

8

Reactant 2

HCID 2900864-bromo-6,7-dimethoxy-1-indanoneHCID 178418546HCID 178418546, compound

Product 1

HCID 19042284HCID 19042284, compound

Reagents, catalysts & solvents 5

HCID 16211236Trichloroiron;hexahydrateCatalystHCID 313Hydrochloric AcidSolventHCID 962WaterSolvent2×HCID 1140TolueneSolvent2×HCID 6228DimethylformamideSolvent

Procedure

A mixture of 6.57 g (24.2 mmol) of 4-bromo-6,7-dimethoxy-1-indanone [Can. J. Chem. 57, 1603 (1979)] and 2.5 g (28 mmol) of copper(I) cyanide in 7 ml of DMF is stirred for 5.75 hours at 170°. The reaction mixture is then cooled to 100° and then 70 ml of toluene and a solution of 9.7 g (36 mmol) of iron(III) chloride hexahydrate in 15.6 ml of water and 3.5 ml of concentrated hydrochloric acid are added in succession thereto. The reaction mixture is then stirred for 30 minutes at 80°, cooled and diluted with toluene and water. The organic phase is separated off, washed with water, a semi-saturated sodium hydrogen carbonate solution and again with water, dried and concentrated by evaporation. The residue is distilled at 150°-160°/0.1 mbar in a bulb tube still and corresponds to starting compound (a), m.p. 150°; IR (CH2Cl2): 2220, 1710 cm-1 ; 1H-NMR (CDCl3): δ=7.33 (s,1H); 4.12 (s,3H); 3.90 (s,3H); 3.19 (m,2H); 2.76 (m,2H).

Workup

  1. temperatureThe reaction mixture is then cooled to 100°
  2. stirringThe reaction mixture is then stirred for 30 minutes at 80°
  3. temperaturecooled
  4. customThe organic phase is separated off
  5. washwashed with water
  6. dry with materiala semi-saturated sodium hydrogen carbonate solution and again with water, dried
  7. concentrationconcentrated by evaporation
  8. distillationThe residue is distilled at 150°-160°/0.1 mbar in a bulb tube still

Sources & evidence

ORD record
ord-c7ccd7fcd36f4962891724ba98ef8588
Source dataset
uspto-grants-1995_10
Patent number
US05461076

Reaction notes

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