Potassium Iodide → HCID 57656629, compound

HRID 2041147Notes

Reaction equation

HRID 2041147 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 (1.0 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 (1.0 and 9:1)

Sources & evidence

ORD record
ord-864acdb37ab0435b8c3e072f31875014
Source dataset
uspto-grants-2013_11
Patent number
US08580780B2

Reaction notes

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