Potassium Iodide → HCID 57656629, compound

HRID 911260Notes

Reaction equation

HRID 911260 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([OH:9])=[CH:5][CH:4]=1)#[N:2].Br[CH2:11][CH2:12][C:13]([CH3:16])([CH3:15])[CH3:14].C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>CC(C)=O>[CH3:14][C:13]([CH3:16])([CH3:15])[CH2:12][CH2:11][O:9][C:6]1[CH:7]=[CH:8][C:3]([C:1]#[N:2])=[CH:4][CH:5]=1

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 130194-CyanophenolHCID 1371371-Bromo-3,3-dimethylbutane

Product 1

HCID 57656629HCID 57656629, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

Mix 4-cyanophenol (1.2 g, 10 mmol), 1-bromo-3,3-dimethylbutane (5.3 g, 32 mmol), powdered potassium carbonate (4.14 g, 30 mmol), and powdered potassium iodide (166 mg, 1 mmol) in acetone (60 mL). Stir under inert atmosphere and heat at reflux for 48 h. Cool the reaction mixture to ambient temperature. Dilute with acetone, filter and evaporate. Purify by chromatography on silica gel eluting with hexane/EtOAc (10 and 9:1) to obtain the desired intermediate (1.8 g, 89%). MS (ES+) m/z: 221 (M+NH4)+.

Workup

  1. temperatureheat
  2. temperatureat reflux for 48 h
  3. filtrationfilter
  4. customevaporate
  5. customPurify by chromatography on silica gel eluting with hexane/EtOAc (10 and 9:1)

Sources & evidence

ORD record
ord-79e0bde105334bc1a6a905e6f12bbecf
Source dataset
uspto-grants-2011_09
Patent number
US08022062B2

Reaction notes

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