Potassium Iodide → HCID 22117703, compound

HRID 1275687Notes

Reaction equation

HRID 1275687 reaction equation
[N+:1]([C:4]1[CH:17]=[CH:16][CH:15]=[CH:14][C:5]=1[O:6][C:7]1[CH:12]=[CH:11][C:10]([OH:13])=[CH:9][CH:8]=1)([O-:3])=[O:2].[F:18][C:19]1[CH:26]=[CH:25][CH:24]=[CH:23][C:20]=1[CH2:21]Br.[I-].[K+].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.O>[F:18][C:19]1[CH:26]=[CH:25][CH:24]=[CH:23][C:20]=1[CH2:21][O:13][C:10]1[CH:9]=[CH:8][C:7]([O:6][C:5]2[CH:14]=[CH:15][CH:16]=[CH:17][C:4]=2[N+:1]([O-:3])=[O:2])=[CH:12][CH:11]=1

Participants

7

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 67968alpha-Bromo-o-fluorotolueneHCID 12940626HCID 12940626, compound

Product 1

HCID 22117703HCID 22117703, compoundYield 95.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 4-(2-nitrophenoxy)phenol (462 mg, 2.0 mmol) in N,N-dimethylformamide (20 ml) were added 2-fluorobenzyl bromide (400 mg, 2.1 mmol), potassium iodide (40 mg, 0.24 mmol) and potassium carbonate (300 mg, 2.2 mmol), followed by stirring at 50° C. for 4 hours. The reaction solution was poured into water and extracted with ethyl acetate. The organic layer was washed with water and a saturated aqueous sodium chloride solution and dried. The solvent was evaporated under reduced pressure to give 1-[4-(2-fluorobenzyloxy)phenoxy]-2-nitrobenzene (0.65 g).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with water
  3. dry with materiala saturated aqueous sodium chloride solution and dried
  4. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-925e9819806645579bbaadada99959a9
Source dataset
uspto-grants-2000_12
Patent number
US06162832

Reaction notes

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