Sodium Iodide → 4-Benzyloxy-2-fluoro-1-nitrobenzene

HRID 80519

Reaction equation

HRID 80519 reaction equation
Br[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[F:9][C:10]1[CH:11]=[C:12]([OH:19])[CH:13]=[CH:14][C:15]=1[N+:16]([O-:18])=[O:17].C(=O)([O-])[O-].[K+].[K+].[I-].[Na+]>CC(C)=O>[CH2:2]([O:19][C:12]1[CH:13]=[CH:14][C:15]([N+:16]([O-:18])=[O:17])=[C:10]([F:9])[CH:11]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 5209483-Fluoro-4-nitrophenol

Product 1

HCID 221807044-Benzyloxy-2-fluoro-1-nitrobenzene

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
55 °C

Procedure

(Bromomethyl)benzene (10.9 g, 63.7 mmol) and 3-fluoro-4-nitrophenol (10 g, 63.7 mmol) were added to 150 mL acetone followed by potassium carbonate (8.8 g, 63.7 mmol) and sodium iodide (9.54 g, 63.7 mmol). The reaction mixture was heated at 55° C. overnight. The resulting mixture was filtered and concentrated. The crude material was recrystallized in ethyl acetate/hexane to give the title compound. MS (DCI+) m/z 264.9 (M+NH4)+.

Workup

  1. filtrationThe resulting mixture was filtered
  2. concentrationconcentrated
  3. customThe crude material was recrystallized in ethyl acetate/hexane

Sources & evidence

ORD record
ord-9602a878ebc942c498254a3c05a59c9e
Source dataset
uspto-grants-2014_09
Patent number
US08846663B2

Linked notes

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