Water → 2-[2-(4-Bromophenyl)-2-oxoethyl]cycloheptan-1-one

HRID 1973468Notes

Reaction equation

HRID 1973468 reaction equation
[Br:1][C:2]1[CH:11]=[CH:10][C:5]([C:6](=[O:9])[CH2:7]Br)=[CH:4][CH:3]=1.N1([C:17]2[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH:18]=2)CCCC1.[OH2:24]>CN(C)C=O>[Br:1][C:2]1[CH:11]=[CH:10][C:5]([C:6](=[O:9])[CH2:7][CH:18]2[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][C:17]2=[O:24])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 74544-Bromophenacyl bromideHCID 5860371-(1-Pyrrolidinyl)-1-cycloheptene

Product 1

HCID 214915222-[2-(4-Bromophenyl)-2-oxoethyl]cycloheptan-1-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of 80 g (0.28 mole) of p-bromophenacyl bromide in dry dimethylformamide is added dropwise to a cooled solution of 40.2 g (0.28 mole) of 1-pyrrolidino-1-cycloheptene in dry dimethylformamide. After stirring at ambient temperature for 24 hours, and at 100° C. for 5 hours, water is added and the mixture is stirred for an additional 4 hours. The reaction mixture is poured into 1500 ml. of water and extracted with chloroform. The chloroform solution is washed with water, dried, and evaporated to a red oil which is stirred at 100° for 1 hour under a high vacuum. Upon cooling the oil converts to a semi-solid. The semi-solid is crystallized from an ethanol - cyclohexane mixture to give 2-(p-bromophenacyl)cycloheptanone, m.p. 124°-127° C.

Workup

  1. waitat 100° C. for 5 hours
  2. stirringthe mixture is stirred for an additional 4 hours
  3. additionThe reaction mixture is poured into 1500 ml
  4. extractionof water and extracted with chloroform
  5. washThe chloroform solution is washed with water
  6. customdried
  7. customevaporated to a red oil which
  8. stirringis stirred at 100° for 1 hour under a high vacuum
  9. temperatureUpon cooling the oil converts to a semi-solid
  10. customThe semi-solid is crystallized from an ethanol - cyclohexane mixture

Sources & evidence

ORD record
ord-ddc7babab2644f70ae3cf849b98f8eb4
Source dataset
uspto-grants-1976_12
Patent number
US03997557

Reaction notes

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