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

HRID 1430418Notes

Reaction equation

HRID 1430418 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-36111e3a7df94f0c88679ea55cd1d94a
Source dataset
uspto-grants-2015_01
Patent number
US08940889B2

Reaction notes

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