Water → HCID 69103961, compound

HRID 2220413Notes

Reaction equation

HRID 2220413 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8]Cl)=[C:4]([O:10][CH:11]2[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]2)[CH:3]=1.[I-].[K+].[C-:19]#[N:20].[K+].O>C(O)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:19]#[N:20])=[C:4]([O:10][CH:11]2[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]2)[CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 4875Potassium IodideHCID 9032Potassium CyanideHCID 69103680HCID 69103680, compound

Product 1

HCID 69103961HCID 69103961, compoundYield 27.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of 4-bromo-1-chloromethyl-2-cyclohexyloxybenzene (5.58 g) in ethanol (55.8 ml) were added potassium iodide (3.36 g) and potassium cyanide (1.56 g) at room temperature under nitrogen, and the mixture was stirred at 70° C. for 80 minutes. The resulting mixture was poured into water and the aqueous layer was extracted with toluene. The organic layer was washed successively with water and brine, dried over anhydrous magnesium sulfate and evaporated under reduced pressure. The residue was purified by column chromatography on silica gel (hexane/toluene=2:1 to 1:1) to give (4-bromo-2-cyclohexyloxyphenyl)acetonitrile (1.51 g).

Workup

  1. extractionthe aqueous layer was extracted with toluene
  2. washThe organic layer was washed successively with water and brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customevaporated under reduced pressure
  5. customThe residue was purified by column chromatography on silica gel (hexane/toluene=2:1 to 1:1)

Sources & evidence

ORD record
ord-f61549be4a3048b6850b2c2020f71311
Source dataset
uspto-grants-2008_08
Patent number
US07417060B2

Reaction notes

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