Diethyl Ether → HCID 66720797, compound

HRID 1040361Notes

Reaction equation

HRID 1040361 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[C:13]([N+:15]([O-])=O)[CH:12]=[CH:11][C:10]=1[C:18]([F:21])([F:20])[F:19])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CCOCC.C([O-])([O-])=O.[Na+].[Na+]>CCO.CC(O)=O.O.[Fe]>[CH2:1]([O:8][C:9]1[CH:14]=[C:13]([CH:12]=[CH:11][C:10]=1[C:18]([F:19])([F:20])[F:21])[NH2:15])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

8

Reactant 3

HCID 3283Diethyl EtherHCID 10340Sodium CarbonateHCID 66720873HCID 66720873, compound

Product 1

HCID 66720797HCID 66720797, compoundYield 60.3%

Reagents, catalysts & solvents 4

HCID 23925IronCatalystHCID 176Acetic AcidSolventHCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

Add 14.1 g (252 mmol) of iron filings to a mixture of 15 g (50.3 mmol) of 2-(benzyloxy)-4-nitro-1-(trifluoromethyl)benzene in 200 mL of EtOH, 10 mL of AcOH and 100 mL of water, then stir the reaction mixture vigorously at 70° C. for 20 minutes. After cooling to RT, slowly add the reaction mixture to a mixture of 300 mL of ether and 1 L of a saturated aqueous solution of Na2CO3. After neutralizing, extract the aqueous phase again with 2×100 mL of ether. Combine the organic phases, wash with 100 mL of water, dry over calcium chloride and concentrate under reduced pressure. Purify the residue obtained by silica gel column chromatography, eluting with a pentane/EtOAc gradient from 0 to 50% of EtOAc. After concentration under reduced pressure, we obtain 8.1 g of 3-(benzyloxy)-4-(trifluoromethyl)aniline in the form of oil.

Workup

  1. temperatureAfter cooling to RT
  2. additionslowly add the reaction mixture
  3. extractionextract the aqueous phase again with 2×100 mL of ether
  4. washwash with 100 mL of water
  5. dry with materialdry over calcium chloride
  6. concentrationconcentrate under reduced pressure
  7. customPurify the residue
  8. customobtained by silica gel column chromatography
  9. washeluting with a pentane/EtOAc gradient from 0 to 50% of EtOAc
  10. concentrationAfter concentration under reduced pressure, we

Sources & evidence

ORD record
ord-c55cf9fc0f0b432ebccb94adfc2b1ca7
Source dataset
uspto-grants-2013_10
Patent number
US08552201B2

Reaction notes

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