Bromine → Ethyl 3-bromo-4-oxocyclohexane-1-carboxylate

HRID 1856530Notes

Reaction equation

HRID 1856530 reaction equation
[CH2:1]([O:3][C:4]([CH:6]1[CH2:11][CH2:10][C:9](=[O:12])[CH2:8][CH2:7]1)=[O:5])[CH3:2].[Br:13]Br>CCOCC>[CH2:1]([O:3][C:4]([CH:6]1[CH2:11][CH2:10][C:9](=[O:12])[CH:8]([Br:13])[CH2:7]1)=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 24408BromineHCID 317638Ethyl 4-oxocyclohexanecarboxylate

Product 1

HCID 12917737Ethyl 3-bromo-4-oxocyclohexane-1-carboxylate

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a 1 l. three-necked flask provided with a stirrer, condenser and dropping funnel and containing a solution of 25.5 g. of 4-ketocyclohexanecarboxylic acid ethyl ester in 450 ml. of anhydrous ether cooled to -10° was added dropwise over 45 minutes 24 g. of bromine. The resulting colorless solution was washed with 3×100 ml. of water, then with 2×50 ml. of 5% sodium bicarbonate solution and finally with 2×100 ml. of water. The ether solution was dried over anhydrous magnesium sulfate and then the solvent was removed on a steam bath. The yield of crude 3-bromo-4-ketocyclohexanecarboxylic acid ethyl ester was 37 g.

Workup

  1. customthree-necked flask provided with a stirrer, condenser
  2. additioncontaining a solution of 25.5 g
  3. additionwas added dropwise over 45 minutes 24 g
  4. washThe resulting colorless solution was washed with 3×100 ml
  5. dry with materialThe ether solution was dried over anhydrous magnesium sulfate
  6. customthe solvent was removed on a steam bath

Sources & evidence

ORD record
ord-c3bdbedcd1a648c796732e5d7182b8da
Source dataset
uspto-grants-1980_08
Patent number
US04219657

Reaction notes

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