Iodoethane → HCID 70976042, compound

HRID 1023585Notes

Reaction equation

HRID 1023585 reaction equation
[OH:1][C:2]1[CH:9]=[C:8]([O:10][C:11]2[CH:16]=[CH:15][C:14]([N+:17]([O-:19])=[O:18])=[CH:13][CH:12]=2)[CH:7]=[CH:6][C:3]=1[C:4]#[N:5].C([O-])([O-])=O.[K+].[K+].I[CH2:27][CH3:28]>CN(C=O)C>[CH2:27]([O:1][C:2]1[CH:9]=[C:8]([O:10][C:11]2[CH:16]=[CH:15][C:14]([N+:17]([O-:19])=[O:18])=[CH:13][CH:12]=2)[CH:7]=[CH:6][C:3]=1[C:4]#[N:5])[CH3:28]

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 67235855HCID 67235855, compound2×

Product 1

HCID 70976042HCID 70976042, compoundYield 87.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-hydroxy-4-[(4-nitrophenyl)oxy]benzonitrile (Intermediate 127, 87.2 mg) was dissolved in DMF (5 mL). K2CO3 (92.2 mg, 0.67 mmol) and iodoethane (32 μL, 0.40 mmol) were added. The reaction mixture was stirred at r.t. After 16 h, the reaction mixture was evaporated to dryness to give the crude product that was purified by silica gel chromatography (from 100:0 to 50:50 Cyclohexane/EtOAc in 10 CV; then 50:50 Cyclohexane/EtOAc for 10 CV) to obtain 84.9 mg of the title compound as a yellow solid.

Workup

  1. customthe reaction mixture was evaporated to dryness
  2. customto give the crude product that
  3. customwas purified by silica gel chromatography (from 100:0 to 50:50 Cyclohexane/EtOAc in 10 CV

Sources & evidence

ORD record
ord-16bdad1541624927a2aff3f3d5420948
Source dataset
uspto-grants-2014_05
Patent number
US08722695B2

Reaction notes

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