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

HRID 619105Notes

Reaction equation

HRID 619105 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 liter 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-0d29853eb1df4f9bbbc87be44da6c75a
Source dataset
uspto-grants-1999_09
Patent number
US05958927

Reaction notes

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