2-Fluoro-5-nitroaniline → 1-(2-fluoro-5-nitrophenyl)-1H-pyrrole

HRID 508273Notes

Reaction equation

HRID 508273 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([F:11])=[C:8]([CH:10]=1)[NH2:9])([O-:3])=[O:2].CO[CH:14]1[CH2:18][CH2:17][CH:16](OC)O1>C(O)(=O)C>[F:11][C:7]1[CH:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:10][C:8]=1[N:9]1[CH:14]=[CH:18][CH:17]=[CH:16]1

Participants

4

Reactant 2

HCID 677852-Fluoro-5-nitroanilineHCID 790982,5-Dimethoxytetrahydrofuran

Product 1

HCID 27811271-(2-fluoro-5-nitrophenyl)-1H-pyrroleYield 78%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
110 °C

Procedure

5-Nitro-2-fluoroaniline (7.0 g, 44.8 mmol) was taken up in acetic acid (60 mL) in a 250 mL round bottomed flask and treated with 2,5-dimethoxytetrahydrofuran (6.3 mL, 49.8 mmol). The resulting mixture was heated to 110° C. for 4 hours. TLC analysis indicated complete conversion of starting material to product after 4 hours. Thus, the reaction mixture was cooled to ambient temperature, transferred to a separatory funnel and partitioned (CH2Cl2//H2O). The organic phase was washed with H2O (3×50 mL), brine (3×50 mL), dried over Na2SO4 and evaporated in vacuo to give a light brown residue. The residue was purified by flash chromatography (hexanes→1:9 EtOAc/hexanes) to afford the title compound as a light yellow solid (7.2 g, 78%).

Workup

  1. customafter 4 hours
  2. temperatureThus, the reaction mixture was cooled to ambient temperature
  3. customtransferred to a separatory funnel
  4. custompartitioned (CH2Cl2//H2O)
  5. washThe organic phase was washed with H2O (3×50 mL), brine (3×50 mL)
  6. dry with materialdried over Na2SO4
  7. customevaporated in vacuo
  8. customto give a light brown residue
  9. customThe residue was purified by flash chromatography (hexanes→1:9 EtOAc/hexanes)

Sources & evidence

ORD record
ord-7b1bd42e050b4a23b1de94453c3f4af0
Source dataset
uspto-grants-2015_08
Patent number
US09095593B2

Reaction notes

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