N-bromobutanimide → Ethyl 3-bromo-4-oxocyclohexane-1-carboxylate

HRID 524413Notes

Reaction equation

HRID 524413 reaction equation
[Br:1]N1C(=O)CCC1=O.[CH2:9]([O:11][C:12]([CH:14]1[CH2:19][CH2:18][C:17](=[O:20])[CH2:16][CH2:15]1)=[O:13])[CH3:10]>C1(C)C=CC=CC=1.CC1C=CC(S(O)(=O)=O)=CC=1>[CH2:9]([O:11][C:12]([CH:14]1[CH2:19][CH2:18][C:17](=[O:20])[CH:16]([Br:1])[CH2:15]1)=[O:13])[CH3:10]

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 317638Ethyl 4-oxocyclohexanecarboxylate

Product 1

HCID 12917737Ethyl 3-bromo-4-oxocyclohexane-1-carboxylateYield 140.8%

Reagents, catalysts & solvents 2

HCID 6101p-Toluenesulfonic acidCatalystHCID 1140TolueneSolvent

Procedure

To a stirred solution of N-bromosuccinimide (1.11 g, 6.274 mmol), PTSA (0.108 g, 0.627 mmol) in toluene (15 mL) was added 4-oxocyclohexanecarboxylic acid ethyl ester (1.068 g, 6.274 mmol) under nitrogen atmosphere and the reaction was refluxed for 2 hrs. Toluene was evaporated under reduced pressure and the residue was partitioned between water (50 mL) and ethyl acetate (50 mL). The layers were separated; the organic layer was washed with sat. sodium bicarbonate solution followed by brine, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to get title the compound (2.2 g) which was carried without purification for the next step.

Workup

  1. temperaturethe reaction was refluxed for 2 hrs
  2. customToluene was evaporated under reduced pressure
  3. customthe residue was partitioned between water (50 mL) and ethyl acetate (50 mL)
  4. customThe layers were separated
  5. washthe organic layer was washed with sat. sodium bicarbonate solution
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-32c34edfc985463ca8545d3fd3a48dc1
Source dataset
uspto-grants-2016_05
Patent number
US09340506B2

Reaction notes

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