Potassium Carbonate → Ethyl 4-[(4-bromophenyl)thio]-3-oxocyclohexanecarboxylate

HRID 1593642Notes

Reaction equation

HRID 1593642 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([SH:8])=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].Br[CH:16]1[CH2:21][CH2:20][CH:19]([C:22]([O:24][CH2:25][CH3:26])=[O:23])[CH2:18][C:17]1=[O:27]>CC(C)=O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][CH:16]2[CH2:21][CH2:20][CH:19]([C:22]([O:24][CH2:25][CH3:26])=[O:23])[CH2:18][C:17]2=[O:27])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 660494-BromothiophenolHCID 12917736Ethyl 4-bromo-3-oxocyclohexanecarboxylate

Product 1

HCID 69249727Ethyl 4-[(4-bromophenyl)thio]-3-oxocyclohexanecarboxylateYield 63.4%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

To a solution of 4-bromobenzenethiol (2.92 g, 15.45 mmol) in 20 mL acetone was added K2CO3 (2.2 g, 15.18 mmol) and a solution of ethyl 4-bromo-3-oxocyclohexanecarboxylate (3.73 g, 15 mmol) in acetone (10 mL). The resulting suspension was stirred at room temperature for 2 hour, and then was partitioned between water and hexane. The organic layer was washed with water, then brine, then was dried over MgSO4, filtered, and concentrated. Purification by chromatography on silica gel (15% EtOAc in hexane) afforded 3.4 g (61%) of the title compound as an oil: MS (ES) m/z=356 [M]+.

Workup

  1. customwas partitioned between water and hexane
  2. washThe organic layer was washed with water
  3. dry with materialbrine, then was dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customPurification by chromatography on silica gel (15% EtOAc in hexane)

Sources & evidence

ORD record
ord-777c705b79ad4b9abdb9db43c20725ea
Source dataset
uspto-grants-2007_11
Patent number
US07297704B2

Reaction notes

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