3-Methoxy-5-nitrobenzotrifluoride → 3-Hydroxy-5-nitrobenzotrifluoride

HRID 887659Notes

Reaction equation

HRID 887659 reaction equation
C[O:2][C:3]1[CH:8]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:6]=[C:5]([N+:13]([O-:15])=[O:14])[CH:4]=1.N1C=CC=CC=1.Cl>C(Cl)Cl>[N+:13]([C:5]1[CH:4]=[C:3]([OH:2])[CH:8]=[C:7]([C:9]([F:10])([F:11])[F:12])[CH:6]=1)([O-:15])=[O:14]

Participants

4

Reactant 2

HCID 5205973-Methoxy-5-nitrobenzotrifluorideHCID 10176127Pyridinium chloride

Product 1

HCID 27562513-Hydroxy-5-nitrobenzotrifluoride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A flask containing 1-Methoxy-3-nitro-5-trifluoromethyl-benzene (10 g) and hydrochloride pyridine (10 eq, 52.0 g) was heated to 210 C and stirred for 12 h. Once complete, the reaction was cooled and the residue was dissolved in CH2Cl2 and washed twice with water (100 mL). The organic layer was concentrated under vacuum and then set in the freezer overnight. The resulting crystalline product was filtered off and washed with ether and used as is.

Workup

  1. temperaturewas heated to 210 C
  2. temperatureOnce complete, the reaction was cooled
  3. washwashed twice with water (100 mL)
  4. concentrationThe organic layer was concentrated under vacuum
  5. customset in the freezer overnight
  6. filtrationThe resulting crystalline product was filtered off
  7. washwashed with ether

Sources & evidence

ORD record
ord-6046d88f40ed42618bf626c2c50518c9
Source dataset
uspto-grants-2012_08
Patent number
US08247430B2

Reaction notes

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