3-(Trifluoromethyl)phenol → HCID 288110, compound

HRID 555396Notes

Reaction equation

HRID 555396 reaction equation
Cl[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[C:4](OC)[N:3]=1.[F:13][C:14]([F:23])([F:22])[C:15]1[CH:16]=[C:17]([OH:21])[CH:18]=[CH:19][CH:20]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C>[N+:8]([C:7]1[C:2]([O:21][C:17]2[CH:18]=[CH:19][CH:20]=[C:15]([C:14]([F:13])([F:22])[F:23])[CH:16]=2)=[N:3][CH:4]=[CH:5][CH:6]=1)([O-:10])=[O:9]

Participants

5

Reactant 3

HCID 73763-(Trifluoromethyl)phenolHCID 10796Cesium carbonateHCID 27950292-Chloro-6-methoxy-3-nitropyridine

Product 1

HCID 288110HCID 288110, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

A solution of 2-chloro-6-methoxy-3-nitropyridine (20 g, 125 mmol) in DMF (120 mL) was treated with 3-trifluoromethylphenol (21 g, 129 mmol) and cesium carbonate (50 g, 154 mmol). The mixture was heated at 70° C. for 14 h. The reaction was concentrated. The residue was dissolved in ethyl acetate and washed with brine, 5% lithium chloride, and aqueous HCl and brine. After concentration, purification was achieved by column chromatography on silica gel using a continuous gradient from 0% to 40% ethyl acetate in hexanes as eluent afforded 21 g (60% yield) of 3a as a white crystals. [M+H]+=285.17.

Workup

  1. concentrationThe reaction was concentrated
  2. dissolutionThe residue was dissolved in ethyl acetate
  3. washwashed with brine, 5% lithium chloride, and aqueous HCl and brine
  4. concentrationAfter concentration, purification

Sources & evidence

ORD record
ord-607b51f8ecfa4c09b875d9f1fed5c434
Source dataset
uspto-grants-2011_11
Patent number
US08053450B2

Reaction notes

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