1,2-Dibromoethane → ((2-Bromoethyl)thio)cyclohexane

HRID 660046Notes

Reaction equation

HRID 660046 reaction equation
[Br:1][CH2:2][CH2:3]Br.C([O-])([O-])=O.[K+].[K+].[CH:11]1([SH:17])[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1>CN(C=O)C.C(OCC)C>[Br:1][CH2:2][CH2:3][S:17][CH:11]1[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1

Participants

6

Reactant 3

HCID 78391,2-DibromoethaneHCID 11430Potassium CarbonateHCID 15290Cyclohexanethiol

Product 1

HCID 22455667((2-Bromoethyl)thio)cyclohexane

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

19.4 ml (225.0 mmol) of 1,2-dibromoethane and 4.1 g (30.0 mmol) of K2CO3 were added to a solution of 3.7 ml (30.0 mmol) of cyclohexanethiol in DMF (46 ml). After 2 hours of stirring at RT, the mixture was diluted with diethyl ether (200 ml) and washed with saturated aqueous NaCl solution. The organic phase was dried over MgSO4, filtered and concentrated in vacuo. The resulting 6.1 g of crude product (2-bromoethyl)(cyclohexyl)sulfane were used for the further reaction without being purified further.

Workup

  1. washwashed with saturated aqueous NaCl solution
  2. dry with materialThe organic phase was dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe resulting 6.1 g of crude product (2-bromoethyl)(cyclohexyl)sulfane were used for the further reaction
  6. customwithout being purified further

Sources & evidence

ORD record
ord-dd396bdeb76849959566f21f60b0b23d
Source dataset
uspto-grants-2011_12
Patent number
US08084470B2

Reaction notes

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