Ethyl Bromide → Ethyl 4-cyanophenyl sulfide

HRID 911283Notes

Reaction equation

HRID 911283 reaction equation
[SH:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=1.Br[CH2:11][CH3:12].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH2:11]([S:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=1)[CH3:12]

Participants

5

Reactant 3

HCID 6332Ethyl BromideHCID 11430Potassium CarbonateHCID 5850584-Thiobenzonitrile

Product 1

HCID 21262891Ethyl 4-cyanophenyl sulfideYield 83%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Combine 4-mercapto-benzonitrile (0.4 g, 2.96 mmol), bromoethane (1.4 mL, 8.88 mmol) and potassium carbonate (3.3 g, 23.7 mmol) in anhydrous DMF (7 mL) and heat at 60° C. for 17 h. Cool the reaction mixture to ambient temperature and partition between brine (20 mL) and EtOAc (20 mL). Separate the organic layer, dry over anhydrous Na2SO4 and concentrate. Purify by chromatography on silica gel eluting with hexane/EtOAc (1:0, 9:1 and 4:1) to obtain the desired intermediate as a colorless oil (0.4 g, 83%).

Workup

  1. custompartition between brine (20 mL) and EtOAc (20 mL)
  2. customSeparate the organic layer
  3. dry with materialdry over anhydrous Na2SO4
  4. concentrationconcentrate
  5. customPurify by chromatography on silica gel eluting with hexane/EtOAc (1:0, 9:1 and 4:1)

Sources & evidence

ORD record
ord-c3aa0a5f7356458d8baf58e3291c277f
Source dataset
uspto-grants-2011_09
Patent number
US08022062B2

Reaction notes

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