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

HRID 1593620Notes

Reaction equation

HRID 1593620 reaction equation
[O:1]=[C:2]1[CH2:7][CH2:6][CH:5]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH2:4][CH2:3]1.[Br:13]Br.C([O-])(O)=O.[Na+]>C(OCC)C.O>[Br:13][CH:3]1[C:2](=[O:1])[CH2:7][CH2:6][CH:5]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH2:4]1

Participants

6

Reactant 3

HCID 24408BromineHCID 317638Ethyl 4-oxocyclohexanecarboxylateHCID 516892Sodium Bicarbonate

Product 1

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

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent2×

Procedure

To a 0° C. solution of ethyl 4-oxocyclohexanecarboxylate (6.0 g, 35.3 mmol) in diethyl ether (200 mL) was added dropwise a solution of bromine (5.3 g, 33.3 mmol) in diethyl ether (20 mL). The resulting mixture was stirred at room temperature for 40 min, then was cooled in an ice/water bath, diluted with water, and neutralized with aqueous NaHCO3 solution. The organic layer was separated and washed with water then brine, then was dried over MgSO4 and concentrated to an oil, which was used in next reaction without purification.

Workup

  1. temperaturewas cooled in an ice/water bath
  2. customThe organic layer was separated
  3. washwashed with water
  4. dry with materialbrine, then was dried over MgSO4
  5. concentrationconcentrated to an oil, which
  6. customwas used in next reaction without purification

Sources & evidence

ORD record
ord-93474b6534974c0ba2187751fcc1428f
Source dataset
uspto-grants-2007_11
Patent number
US07297704B2

Reaction notes

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