Sodium Iodide → HCID 59191332, compound

HRID 1023936Notes

Reaction equation

HRID 1023936 reaction equation
[CH2:1]([C:3]1[CH:17]=[CH:16][C:6]([O:7][C:8]2[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][C:9]=2[F:15])=[C:5]([O:18][CH3:19])[CH:4]=1)[CH3:2].[OH-].[K+].[Na+].[I-].Br[CH2:25][CH2:26][CH2:27][N:28]1[C:32](=[O:33])[C:31]2=[CH:34][CH:35]=[CH:36][CH:37]=[C:30]2[C:29]1=[O:38]>CC(C)=O>[CH2:1]([C:3]1[CH:17]=[CH:16][C:6]([O:7][C:8]2[CH:13]=[CH:12][C:11]([O:14][CH2:25][CH2:26][CH2:27][N:28]3[C:32](=[O:33])[C:31]4[C:30](=[CH:37][CH:36]=[CH:35][CH:34]=4)[C:29]3=[O:38])=[CH:10][C:9]=2[F:15])=[C:5]([O:18][CH3:19])[CH:4]=1)[CH3:2]

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 14797Potassium HydroxideHCID 21611N-3-BromopropylphthalimideHCID 59191360HCID 59191360, compound

Product 1

HCID 59191332HCID 59191332, compoundYield 53.1%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 4-(4-ethyl-2-methoxyphenoxy)-3-fluorophenol (0.32 mmol; 85 mg) in dry acetone (3 mL), under argon, were added potassium hydroxide (0.39 mmol; 54 mg), NaI (0.065 mmol; 10 mg) and N-(3-bromopropyl)phtalimide (0.40 mmol; 107 mg). The reaction was stirred 3 days at 50° C. The mixture was concentrated in vacuo, hydrolysed with NH4Cl sat.(5 mL) and extracted with ethyl acetate (3*3 mL). Combined organic phases were dried over Na2SO4, concentrated in vacuo. The title compound (75 mg; 0.17 mmol; 51%) was obtained as an oil, after purification by preparative TLC (cyclohexane/ethyl acetate: 7/3).

Workup

  1. concentrationThe mixture was concentrated in vacuo, hydrolysed with NH4Cl sat.(5 mL)
  2. extractionextracted with ethyl acetate (3*3 mL)
  3. dry with materialCombined organic phases were dried over Na2SO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-84b342b3a26a4cf58524777d9d5b8c3d
Source dataset
uspto-grants-2014_05
Patent number
US08722746B2

Reaction notes

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