Acetic Acid → 3-Hydroxy-5-nitrobenzotrifluoride

HRID 1994114Notes

Reaction equation

HRID 1994114 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([O:14]C2C=C(C(F)(F)F)C=C([N+]([O-])=O)C=2)[CH:7]=[C:8]([C:10]([F:13])([F:12])[F:11])[CH:9]=1)([O-:3])=[O:2].CC(O)=O>Br>[N+:1]([C:4]1[CH:5]=[C:6]([OH:14])[CH:7]=[C:8]([C:10]([F:11])([F:12])[F:13])[CH:9]=1)([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 176Acetic AcidHCID 152723991,1'-Oxybis[3-nitro-5-(trifluoromethyl)benzene]

Product 1

HCID 27562513-Hydroxy-5-nitrobenzotrifluorideYield 100.3%

Reagents, catalysts & solvents 1

HCID 260Hydrogen BromideCatalyst

Procedure

A solution of 3-nitro-5-(trifluoromethyl)phenyl ether (20.0 g, 0.090 mol) in HBr (74.7 mL, 1.38 mmol) and HOAc (279.8 mL, 4.92 mol) was heated at reflux until reaction was judged to be complete by LCMS. The reaction was concentrated to tan solid to yield the desired product (18.7 g, 96% yield). LCMS: (FA) ES− 206.2 (M−1).

Workup

  1. temperatureat reflux until reaction
  2. concentrationThe reaction was concentrated to tan solid

Sources & evidence

ORD record
ord-c04a532d48c241318bbc9afaea34d41b
Source dataset
uspto-grants-2010_01
Patent number
US07652041B2

Reaction notes

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