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

HRID 2251867Notes

Reaction equation

HRID 2251867 reaction equation
C[O:2][C:3]1[CH:4]=[C:5]([C:12]([F:15])([F:14])[F:13])[CH:6]=[C:7]([N+:9]([O-:11])=[O:10])[CH:8]=1.Cl.[NH+]1C=CC=CC=1>>[OH:2][C:3]1[CH:4]=[C:5]([C:12]([F:13])([F:14])[F:15])[CH:6]=[C:7]([N+:9]([O-:11])=[O:10])[CH:8]=1

Participants

3

Reactant 2

HCID 5205973-Methoxy-5-nitrobenzotrifluorideHCID 21584435Pyridinium hydrochloride

Product 1

HCID 27562513-Hydroxy-5-nitrobenzotrifluoride

Procedure

3-Methoxy-5-nitrobenzotrifluoride (40 g, 181 mmol, 1 eq) and pyridinium hydrochloride (167 g, 1448 mmol, 8 eq) were heated together to 210° C. in an open vessel for 2.5 h. The dark mixture was cooled and partitioned between EtOAc and 2 N HCl. The EtOAc layer was washed (6×) with 2 N HCl, and once with brine. After drying over Na2SO4 the solution was filtered and stripped. The crude material was placed under vacuum for 7 days to provide a brownish solid which was used without further purification.

Workup

  1. temperatureThe dark mixture was cooled
  2. custompartitioned between EtOAc and 2 N HCl
  3. washThe EtOAc layer was washed (6×) with 2 N HCl
  4. dry with materialAfter drying over Na2SO4 the solution
  5. filtrationwas filtered
  6. customto provide a brownish solid which
  7. customwas used without further purification

Sources & evidence

ORD record
ord-373fe082206749f68200aa2291154edc
Source dataset
uspto-grants-2008_01
Patent number
US07320992B2

Reaction notes

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