6-Methoxy-1-Indanone → 2-Bromo-6-methoxy-1-indanone

HRID 1107418Notes

Reaction equation

HRID 1107418 reaction equation
[Br-:1].[Br-].[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C([N+](CCCC)(CCCC)CCCC)CCC.C([N+](CCCC)(CCCC)CCCC)CCC.[CH3:55][O:56][C:57]1[CH:65]=[C:64]2[C:60]([CH2:61][CH2:62][C:63]2=[O:66])=[CH:59][CH:58]=1>CO.ClCCl>[Br:1][CH:62]1[CH2:61][C:60]2[C:64](=[CH:65][C:57]([O:56][CH3:55])=[CH:58][CH:59]=2)[C:63]1=[O:66]

Participants

5

Reactant 2

HCID 3340366-Methoxy-1-IndanoneHCID 23500184Tetra-n-butylammonium tribromide

Product 1

HCID 110967482-Bromo-6-methoxy-1-indanone

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

49.2 g (102 mmol) of tetra-n-butylammonium tribromide are added in fractions over the course of 15 minutes, at room temperature, to 16.2 g (100 mmol) of 6-methoxy-indan-1-one dissolved in 400 ml of methanol and 1 litre of dichloromethane, and the mixture is then stirred overnight at room temperature. After evaporation, the residue is taken up in 500 ml of dichloromethane and washed twice with 250 ml of N hydrochloric acid. Drying over magnesium sulphate and concentration, and then rapid filtration over 500 g of silica (eluant:dichloromethane) yield 23.4 g of the desired product.

Workup

  1. customAfter evaporation
  2. washwashed twice with 250 ml of N hydrochloric acid
  3. dry with materialDrying over magnesium sulphate and concentration
  4. filtrationrapid filtration over 500 g of silica (eluant:dichloromethane) yield 23.4 g of the desired product

Sources & evidence

ORD record
ord-054e6b1ca4804991a8d0d44ba4a7deae
Source dataset
uspto-grants-2000_05
Patent number
US06060487

Reaction notes

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