Cyclohexyl bromide → HCID 69119835, compound

HRID 2118332Notes

Reaction equation

HRID 2118332 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([SH:8])[CH:5]=[CH:6][CH:7]=1.[CH:9]1(Br)[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH:9]1([S:8][C:4]2[CH:5]=[CH:6][CH:7]=[C:2]([Br:1])[CH:3]=2)[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1

Participants

5

Reactant 3

HCID 7960Cyclohexyl bromideHCID 11430Potassium CarbonateHCID 80597m-Bromobenzenethiol

Product 1

HCID 69119835HCID 69119835, compoundYield 54.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 3-bromobenzenethiol (5.00 g) in DMF (100 ml) was added cyclohexyl bromide (4.31 g) and potassium carbonate (7.31 g). The mixture was stirred at room temperature under nitrogen for 18 h. The reaction mixture was partitioned between 2N HCl and EtOAC. The organic phase was washed with brine and dried (MgSO4). Filtration and removal of the solvent under reduced pressure gave the title compound (3.89 g). Tlc (silica) (4:1 cyclohexane-diethyl ether) Rf=0.90.

Workup

  1. customThe reaction mixture was partitioned between 2N HCl and EtOAC
  2. washThe organic phase was washed with brine
  3. dry with materialdried (MgSO4)
  4. filtrationFiltration and removal of the solvent under reduced pressure

Sources & evidence

ORD record
ord-601da84035e347dba30dbad4dd98c46e
Source dataset
uspto-grants-2008_10
Patent number
US07442839B2

Reaction notes

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