2-Bromo-2,3-dihydro-4-fluoro-1H-inden-1-one → 2-Bromo-6,7-dichloro-1-indanone

HRID 1489023Notes

Reaction equation

HRID 1489023 reaction equation
[Br:1]C1CC2C(=CC=CC=2F)C1=O.[Cl:13][C:14]1[C:22]([Cl:23])=[C:21]2[C:17]([CH2:18][CH2:19][C:20]2=[O:24])=[CH:16][CH:15]=1>[Cu](Br)Br.O1CCOCC1>[Br:1][CH:19]1[CH2:18][C:17]2[C:21](=[C:22]([Cl:23])[C:14]([Cl:13])=[CH:15][CH:16]=2)[C:20]1=[O:24]

Participants

5

Reactant 2

HCID 98374932-Bromo-2,3-dihydro-4-fluoro-1H-inden-1-oneHCID 219860816,7-Dichloro-2,3-dihydro-1H-inden-1-one

Product 1

HCID 229036022-Bromo-6,7-dichloro-1-indanone

Reagents, catalysts & solvents 2

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

Procedure

The 2-bromo-6,7-dichloro-1-indanone is prepared as in Example 14 for the preparation of 2-bromo-4-fluoro-1-indanone but starting with 7.42 g of 6,7-dichloro-1-indanone, 21.8 g of copper bromide and 240 ml of dioxane. After purification by silica column chromatography with an ethyl acetate-cyclohexane mixture (10-90 by volume) as eluent, 6.79 g of 2-bromo-6,7-dichloro-1-indanone are obtained which melt at 103° C.

Workup

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

Sources & evidence

ORD record
ord-8c68ecacc0a747d8b97176c79cba8106
Source dataset
uspto-grants-1997_10
Patent number
US05677306

Reaction notes

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