Benzyl Alcohol → 3-(Trifluoromethyl)-4-(benzyloxy)nitrobenzene

HRID 1157153Notes

Reaction equation

HRID 1157153 reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[C:11]([F:14])([F:13])[F:12].[CH2:15]([OH:22])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.[H-].[Na+]>C1COCC1>[CH2:15]([O:22][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[C:11]([F:14])([F:13])[F:12])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 244Benzyl AlcoholHCID 24758Sodium hydrideHCID 949542-Fluoro-5-nitrobenzotrifluoride

Product 1

HCID 219520843-(Trifluoromethyl)-4-(benzyloxy)nitrobenzeneYield 79%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-fluoro-5-nitrobenzotrifluoride (500 mg, 2.48 mmol) and benzyl alcohol (267 mg, 2.48 mmol) in THF was added sodium hydride (95.1 mg, 2.48 mmol) at 0° C. The reaction was followed by TLC and quenched with saturated ammonium chloride solution after 0.5 h. The mixture was extracted with dichloromethane three times. The combined organic layer was dried over sodium sulfate and concentrated. The residue was triturated with 2.5 mL of hexanes and ethyl acetate (7:1) and a yellow precipitate was collected by filtration to give 1-benzyloxy-4-nitro-2-trifluoromethylbenzene (580 mg, 79%).

Workup

  1. customquenched with saturated ammonium chloride solution after 0.5 h
  2. extractionThe mixture was extracted with dichloromethane three times
  3. dry with materialThe combined organic layer was dried over sodium sulfate
  4. concentrationconcentrated
  5. customThe residue was triturated with 2.5 mL of hexanes and ethyl acetate (7:1)
  6. filtrationa yellow precipitate was collected by filtration

Sources & evidence

ORD record
ord-0857f0806883402b9faa01a8551adfb3
Source dataset
uspto-grants-2010_10
Patent number
US07807672B2

Reaction notes

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