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

HRID 2086946Notes

Reaction equation

HRID 2086946 reaction equation
[H-].[Na+].[CH2:3]([OH:10])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[H][H].F[C:14]1[CH:19]=[CH:18][C:17]([N+:20]([O-:22])=[O:21])=[CH:16][C:15]=1[C:23]([F:26])([F:25])[F:24]>CN(C=O)C>[CH2:3]([O:10][C:14]1[CH:19]=[CH:18][C:17]([N+:20]([O-:22])=[O:21])=[CH:16][C:15]=1[C:23]([F:24])([F:25])[F:26])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

6

Reactant 4

HCID 244Benzyl AlcoholHCID 24758Sodium hydrideHCID 949542-Fluoro-5-nitrobenzotrifluorideHCID 178418361HCID 178418361, compound

Product 1

HCID 219520843-(Trifluoromethyl)-4-(benzyloxy)nitrobenzeneYield 83%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

60% NaH dispersion (1.4 g, 33.5 mmol) in mineral oil was washed with hexanes and then suspended in DMF (10 ml). To this NaH suspension in DMF, added benzyl alcohol (2.8 ml, 26.3 mmol) with water bath to keep the temperature below 30° C. The reaction mixture was stirred until the evolution of the hydrogen gas ceased. To a solution of 2-fluoro-5-nitrobenzotrifluoride (5.0 g, 23.9 mmol) in DMF (20 ml) was added the benzyl alkoxide solution slowly at 0° C. Upon the completion of the addition, the ice bath was removed and the reaction mixture was stirred at room temperature for 2 hours. The reaction mixture was poured into 200 ml ice water, stirred until the yellow solid was formed. Filtered and the solid was washed with water and then trituated with pentane. 5.9 g yellow solid was collected (yield: 83%). ESI-MS m/z 298 (M+H)+

Workup

  1. wash60% NaH dispersion (1.4 g, 33.5 mmol) in mineral oil was washed with hexanes
  2. customthe temperature below 30° C
  3. additionUpon the completion of the addition
  4. customthe ice bath was removed
  5. additionThe reaction mixture was poured into 200 ml ice water
  6. stirringstirred until the yellow solid
  7. customwas formed
  8. filtrationFiltered
  9. washthe solid was washed with water
  10. custom5.9 g yellow solid was collected (yield: 83%)

Sources & evidence

ORD record
ord-a7183b1bbbd049dc94e6c06119f0daa8
Source dataset
uspto-grants-2004_04
Patent number
US06727256B1

Reaction notes

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