4-Nitro-3-trifluoromethylphenol → HCID 59678441, compound

HRID 1392562Notes

Reaction equation

HRID 1392562 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][C:5]=1[C:11]([F:14])([F:13])[F:12])([O-:3])=[O:2].[Br-:15].[Br-:16].[Br-].C([N+](C)(C)C)C1C=CC=CC=1.C([N+](C)(C)C)C1C=CC=CC=1.C([N+](C)(C)C)C1C=CC=CC=1.C([O-])([O-])=O.[Ca+2]>CO.C(Cl)Cl>[Br:15][C:6]1[C:5]([C:11]([F:12])([F:13])[F:14])=[C:4]([N+:1]([O-:3])=[O:2])[CH:9]=[C:8]([Br:16])[C:7]=1[OH:10]

Participants

6

Reactant 3

HCID 69314-Nitro-3-trifluoromethylphenolHCID 10112Calcium CarbonateHCID 53442637Benzyltrimethylammoniumtribromide

Product 1

HCID 59678441HCID 59678441, compoundYield 16%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

2-Nitro-5-hydroxybenzotrifluoride (2.0 g, 9.7 mmol) was dissolved in a mixture of MeOH and CH2Cl2 (80 mL, 1:1) at 0° C. Benzyltrimethylammoniumtribromide (7.53 g, 19.3 mmol) and CaCO3 (2.0 g, 19.3 mmol) was added. The reaction mixture was heated at reflux for three days. The reaction was deemed complete by HPLC and LC/MS analysis and quenched by the addition of 1N HCl. The reaction mixture was washed with brine, dried with MgSO4 and purified on column (silica gel, with gradient elution of CHCl3/MeOH). This gave to 550 mg (16%) of 2,6-dibromo-3-trifluoromethyl-4-nitrophenol.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for three days
  3. customquenched by the addition of 1N HCl
  4. washThe reaction mixture was washed with brine
  5. dry with materialdried with MgSO4
  6. custompurified on column (silica gel, with gradient elution of CHCl3/MeOH)

Sources & evidence

ORD record
ord-ece3e89634ee4f8b9af2aee9520aae1f
Source dataset
uspto-grants-2008_03
Patent number
US07342127B2

Reaction notes

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