Bromine → Ethyl 3-bromo-2-oxocyclohexanecarboxylate

HRID 1605091Notes

Reaction equation

HRID 1605091 reaction equation
[CH3:1][CH2:2][O:3][C:4]([CH:6]1[C:11](=[O:12])[CH2:10][CH2:9][CH2:8][CH2:7]1)=[O:5].[Br:13]Br>CCOCC>[CH3:1][CH2:2][O:3][C:4]([CH:6]1[C:11](=[O:12])[CH:10]([Br:13])[CH2:9][CH2:8][CH2:7]1)=[O:5]

Participants

4

Reactant 2

HCID 24408BromineHCID 95543Ethyl 2-oxocyclohexanecarboxylate

Product 1

HCID 121765Ethyl 3-bromo-2-oxocyclohexanecarboxylate

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a stirred solution of 31 g. of ethyl cyclohexanone-2-carboxylate in 25 ml. of ether, cooled to -10° C., was added dropwise 35 g. of bromine. Stirring was continued one hour while the solution was allowed to come to room temperature. The solution was poured into ice water containing 20 g. sodium carbonate and was extracted with ether. The ether extract was washed with water, dried and evaporated to dryness to give 23 g. of the title compound; b.p. 88°-91°C. (0.2 mm).

Workup

  1. additionwas added dropwise 35 g
  2. customto come to room temperature
  3. extractionsodium carbonate and was extracted with ether
  4. extractionThe ether extract
  5. washwas washed with water
  6. customdried
  7. customevaporated to dryness
  8. customto give 23 g

Sources & evidence

ORD record
ord-713020891e1644b1aac311d289f8ba15
Source dataset
uspto-grants-1976_04
Patent number
US03948939

Reaction notes

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