Sodium Trifluoroacetate → 3-Benzyloxy-6-trifluoromethyl-2-nitrotoluene

HRID 565001Notes

Reaction equation

HRID 565001 reaction equation
[CH2:1]([O:8][C:9]1[C:10]([N+:17]([O-:19])=[O:18])=[C:11]([CH3:16])[C:12](Br)=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F:20][C:21]([F:26])([F:25])C([O-])=O.[Na+]>[Cu]I.CN1CCCC1=O>[CH2:1]([O:8][C:9]1[C:10]([N+:17]([O-:19])=[O:18])=[C:11]([CH3:16])[C:12]([C:21]([F:26])([F:25])[F:20])=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 517019Sodium TrifluoroacetateHCID 21194170HCID 21194170, compound

Product 1

HCID 105430343-Benzyloxy-6-trifluoromethyl-2-nitrotoluene

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
160 °C

Procedure

A mixture of 1.50 g (4.66 mmol) of 3-benzyloxy-6-bromo-2-nitrotoluene, 6.33 g (46.6 mmol) of sodium trifluoroacetate, 4.43 g (23.3 mmol) of copper (I) iodide and 80 ml of N-methylpyrrolidone was heated at 160° C. for 7 hours while stirring. Next, the solvent was distilled off under reduced pressure and ethyl acetate was added to the resulting residue. Insoluble matters were then filtered off. The filtrate was washed twice with water. After drying over anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure and the residue was isolated and purified by silica gel column chromatography to give 0.70 (48.3%) of 3-benzyloxy-6-trifluoromethyl-2-nitrotoluene.

Workup

  1. distillationNext, the solvent was distilled off under reduced pressure and ethyl acetate
  2. additionwas added to the resulting residue
  3. filtrationInsoluble matters were then filtered off
  4. washThe filtrate was washed twice with water
  5. dry with materialAfter drying over anhydrous magnesium sulfate
  6. distillationthe solvent was distilled off under reduced pressure
  7. customthe residue was isolated
  8. custompurified by silica gel column chromatography

Sources & evidence

ORD record
ord-a7e9e7777e194a9b98249cb919663a5e
Source dataset
uspto-grants-2001_01
Patent number
US06169107A

Reaction notes

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