Water → 4-(2-Fluoro-phenoxy)-2-nitrotoluene

HRID 1727107Notes

Reaction equation

HRID 1727107 reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[C:4]([N+:9]([O-:11])=[O:10])[CH:3]=1.[F:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[OH:19].C(=O)([O-])[O-].[K+].[K+].O>CN1C(=O)CCC1>[F:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[O:19][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[C:4]([N+:9]([O-:11])=[O:10])[CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 97072-FluorophenolHCID 11430Potassium CarbonateHCID 679654-Fluoro-2-nitrotoluene

Product 1

HCID 575666884-(2-Fluoro-phenoxy)-2-nitrotolueneYield 383.5%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
160 °C

Procedure

To 4-fluoro-2-nitrotoluene (25 g, 0.016 mol), 2-fluorophenol (15.8 mL, 0.017 mol) in NMP (350 mL) was added potassium carbonate (22.27 g, 0.016 mol) and the mixture was stirred at 160° C. for 48 h. After cooling at room temperature, water (350 mL) was added and the solution was extracted into ethyl acetate (2×150 mL). The combined organic extracts were dried over Na2SO4, filtered, concentrated and the residue was purified by flash chromatography eluting with Hex:EtOAc 95:5 to yield 15.17 g of 4-(2-fluoro-phenoxy)-2-nitrotoluene: MS: 248 (M+H).

Workup

  1. temperatureAfter cooling at room temperature
  2. extractionthe solution was extracted into ethyl acetate (2×150 mL)
  3. dry with materialThe combined organic extracts were dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customthe residue was purified by flash chromatography
  7. washeluting with Hex

Sources & evidence

ORD record
ord-629038a7307f4a91bf104580f386266b
Source dataset
uspto-grants-2009_02
Patent number
US07495015B2

Reaction notes

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