Bromine → Ethyl 3-bromo-2-oxocyclohexanecarboxylate

HRID 2076014Notes

Reaction equation

HRID 2076014 reaction equation
[C:1]([CH:6]1[CH2:11][CH2:10][CH2:9][CH2:8][C:7]1=[O:12])([O:3][CH2:4][CH3:5])=[O:2].[Br:13]Br>C(OCC)C>[Br:13][CH:8]1[CH2:9][CH2:10][CH2:11][CH:6]([C:1]([O:3][CH2:4][CH3:5])=[O:2])[C:7]1=[O:12]

Participants

4

Reactant 2

HCID 24408BromineHCID 95543Ethyl 2-oxocyclohexanecarboxylate

Product 1

HCID 121765Ethyl 3-bromo-2-oxocyclohexanecarboxylateYield 102.1%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

2-Carbethoxy-cyclohexanone (5.0 g, 29.4 mmol) was dissolved in diethyl ether (30 mL). To this solution bromine (4.93 g, 30.8 mmol) was added drop wise at room temperature. The reaction was stirred for 1 hour at room temperature, quenched with water and the layers were separated. The organic layer was washed with aqueous thiosulfate solution and brine, dried over sodium sulfate and filtered. The solvent was removed under reduced pressure to yield the crude title compound (7.48 g, 100%) which was used directly in the next step without further purification. 1H NMR (CDCl3, 300 MHz): δ (ppm)=4.94 (t, 1H), 4.20 (q, 1H), 2.37 (dt, 1H), 2.25 (m, 1H), 2.09 (m, 2H), 1.74 (m, 2H), 1.24 (t, 3H).

Workup

  1. customquenched with water
  2. customthe layers were separated
  3. washThe organic layer was washed with aqueous thiosulfate solution and brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-798924a75a0b4247a2285f07bfb1978a
Source dataset
uspto-grants-2011_04
Patent number
US07923450B2

Reaction notes

Loading…