Water → 2-(Benzyloxy)-4-fluoro-1-nitrobenzene

HRID 1642622Notes

Reaction equation

HRID 1642622 reaction equation
C([O-])([O-])=O.[K+].[K+].[F:7][C:8]1[CH:9]=[CH:10][C:11]([N+:15]([O-:17])=[O:16])=[C:12]([OH:14])[CH:13]=1.[CH2:18](Br)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.O>CN(C=O)C>[CH2:18]([O:14][C:12]1[CH:13]=[C:8]([F:7])[CH:9]=[CH:10][C:11]=1[N+:15]([O-:17])=[O:16])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7498Benzyl BromideHCID 99375-Fluoro-2-nitrophenolHCID 11430Potassium Carbonate

Product 1

HCID 110969082-(Benzyloxy)-4-fluoro-1-nitrobenzene

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a suspension of K2CO3 (2.07 g, 15 mmol) in DMF (8 mL) is added 5-fluoro-2-nitrophenol (1.57 g, 10 mmol), followed by benzyl bromide (1.75 g, 10.2 mmol). The mixture is stirred at ambient temperature for 18 h, then poured into water and extracted into EtOAc. The organic phase is washed with water (3×), saturated NaCl (1×) and dried over sodium sulfate. The solvent is removed under reduced pressure and the residual oil filtered through a pad of silica gel using DCM to elute 2-benzyloxy-4-fluoro-1-nitrobenzene as a yellow oil, which slowly solidifies on standing: mp=52-54° C.; 1H NMR (CDCl3) δ 8.03-7.98 (m, 2H), 7.53-7.36 (m, 5H), 6.66 (dd, J=10.17, 2.64 Hz, 1H), 6.81-6.73 (m, 1H), 5.26 (s, 2H).

Workup

  1. extractionextracted into EtOAc
  2. washThe organic phase is washed with water (3×), saturated NaCl (1×)
  3. dry with materialdried over sodium sulfate
  4. customThe solvent is removed under reduced pressure
  5. filtrationthe residual oil filtered through a pad of silica gel
  6. washto elute 2-benzyloxy-4-fluoro-1-nitrobenzene as a yellow oil, which

Sources & evidence

ORD record
ord-60f92cede42840dc8e7731f9652b7bed
Source dataset
uspto-grants-2012_02
Patent number
US08119666B2

Reaction notes

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