2-Bromo-2,3-dihydro-4-fluoro-1H-inden-1-one → 2-Bromo-5,6-dichloro-2,3-dihydro-1H-inden-1-one

HRID 1489024Notes

Reaction equation

HRID 1489024 reaction equation
[Br:1]C1CC2C(=CC=CC=2F)C1=O.[Cl:13][C:14]1[CH:15]=[C:16]2[C:20](=[CH:21][C:22]=1[Cl:23])[C:19](=[O:24])[CH2:18][CH2:17]2>[Cu](Br)Br.O1CCOCC1>[Br:1][CH:18]1[CH2:17][C:16]2[C:20](=[CH:21][C:22]([Cl:23])=[C:14]([Cl:13])[CH:15]=2)[C:19]1=[O:24]

Participants

5

Reactant 2

HCID 98374932-Bromo-2,3-dihydro-4-fluoro-1H-inden-1-oneHCID 229036095,6-Dichloro-2,3-dihydro-1H-inden-1-one

Product 1

HCID 229036012-Bromo-5,6-dichloro-2,3-dihydro-1H-inden-1-one

Reagents, catalysts & solvents 2

HCID 24611Copper bromide (CuBr2)CatalystHCID 312751,4-DioxaneSolvent

Procedure

The 2-bromo-5,6-dichloro-1-indanone is prepared as in Example 14 for the preparation of 2-bromo-4-fluoro-1-indanone but starting with 5.48 g of 5,6-dichloro-1-indanone, 16.1 g of copper bromide and 175 ml of dioxane. After purifying by silica column chromatography with an ethyl acetate-cyclohexane mixture (10-90 by volume) as eluent, 4.07 g of 2-bromo-5,6-dichloro-1-indanone are obtained which melt at 85° C.

Workup

  1. customAfter purifying by silica column chromatography with an ethyl acetate-cyclohexane mixture (10-90 by volume) as eluent

Sources & evidence

ORD record
ord-db5fd7e9c040405d8a81fc57918283c4
Source dataset
uspto-grants-1997_10
Patent number
US05677306

Reaction notes

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