Bromine → HCID 12870627, compound

HRID 1447648Notes

Reaction equation

HRID 1447648 reaction equation
N[CH:2]([C:4](=[O:17])[CH2:5][C:6]([CH3:16])([CH3:15])[CH2:7][C:8]1[CH:13]=[CH:12][C:11]([Cl:14])=[CH:10][CH:9]=1)[CH3:3].[Br:18]Br>C(Cl)(Cl)(Cl)Cl>[Br:18][CH:2]([C:4](=[O:17])[CH2:5][C:6]([CH3:16])([CH3:15])[CH2:7][C:8]1[CH:13]=[CH:12][C:11]([Cl:14])=[CH:10][CH:9]=1)[CH3:3]

Participants

4

Reactant 2

HCID 24408BromineHCID 12870629HCID 12870629, compound

Product 1

HCID 12870627HCID 12870627, compoundYield 99.3%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent2×

Procedure

The ketone (20.0 g; 0.084 mole) was dissolved in carbontetrachloride (200 ml). The solution was cooled on ice and a 10% solution of bromine (0.084 mole) in CCl4 was added at such a rate that the drops were decolourized immediately. The total time of bromination was about 2 hours. After evaporation of the solvent in vacuo a pure oil of 2-bromo-5,5-dimethyl-6-(4-chlorophenyl)-3-hexanone (26.5 g; 99% yield) was obtained. To a solution of the bromoketone (5.0 g; 0.016 mole) in dimethylformamide (20 ml) was added potassium phtalimide (3.2 g; 0.017 mole) in portions under stirring during 5 minutes. The temperature was raised spontaneously to 40° C. Stirring was continued for 15 minutes. Chloroform (30 ml) was added and the mixture was poured into water (100 ml) under stirring. The organic layer was separated and the aqueous phase was washed with CHCl3. The combined chloroform phase was washed with 0.2 N sodium hydroxide solution and water. After drying over anhydrous sodium sulphate and evaporation of the solvent a yellow oil was obtained. The oil crystallized from ethanol-ether affording white crystals of 6-(4-chlorophenyl)-5,5-dimethyl-2-phtalimido-3-hexanone (2.6 g; 43% yield) melting at 96°-98° C.

Workup

  1. temperatureThe solution was cooled on ice

Sources & evidence

ORD record
ord-0219c64eec884e52b8bc1e6b0a6b9a28
Source dataset
uspto-grants-1979_12
Patent number
US04177291

Reaction notes

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