Benzyl Alcohol → 3-benzyloxy-2-nitro-N-methylaniline

HRID 2402554Notes

Reaction equation

HRID 2402554 reaction equation
[CH2:1]([OH:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].C1(C)C=CC=CC=1.F[C:23]1[C:24]([N+:31]([O-:33])=[O:32])=[C:25]([CH:28]=[CH:29][CH:30]=1)[NH:26][CH3:27]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.O>[CH2:1]([O:8][C:23]1[C:24]([N+:31]([O-:33])=[O:32])=[C:25]([CH:28]=[CH:29][CH:30]=1)[NH:26][CH3:27])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 244Benzyl AlcoholHCID 1140TolueneHCID 11430Potassium CarbonateHCID 544897393-fluoro-N-methyl-2-nitroaniline

Product 1

HCID 107298903-benzyloxy-2-nitro-N-methylanilineYield 100%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 962WaterSolvent

Procedure

Benzyl alcohol (9.54 mL, 92.2 mmol), tetrabutyl ammonium bromide (1.49 g, 4.62 mmol), and potassium carbonate (7.64 g, 55.3 mmol) were added to a toluene solution (39 mL) of 3-fluoro-N-methyl-2-nitroaniline (7.84 g, 46.1 mmol), and the mixture was heated under reflux for 6 hours. The reaction solution was cooled, and water (39 mL) was added thereto, followed by toluene extraction. The resulting organic layer was washed with water, and the solvent was distilled off under reduced pressure, thereby obtaining 11.9 g of a red, powdery target compound (yield: 100%).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 6 hours
  3. temperatureThe reaction solution was cooled
  4. extractionfollowed by toluene extraction
  5. washThe resulting organic layer was washed with water
  6. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-b81df3d9fd22458e9729ff16799c0810
Source dataset
uspto-grants-2014_08
Patent number
US08796447B2

Reaction notes

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