4-Nitro-3-trifluoromethylphenol → HCID 22501934, compound

HRID 1814669Notes

Reaction equation

HRID 1814669 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].[CH:15]1([CH2:18]O)[CH2:17][CH2:16]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>C1COCC1>[CH:15]1([CH2:18][O:10][C:7]2[CH:8]=[CH:9][C:4]([N+:1]([O-:3])=[O:2])=[C:5]([C:11]([F:12])([F:13])[F:14])[CH:6]=2)[CH2:17][CH2:16]1

Participants

6

Reactant 4

HCID 69314-Nitro-3-trifluoromethylphenolHCID 11776TriphenylphosphineHCID 75644CyclopropanemethanolHCID 220568ethyl N-ethoxycarbonyliminocarbamate

Product 1

HCID 22501934HCID 22501934, compoundYield 38.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
20 °C

Procedure

1-Nitro-4-hydroxy-2-trifluromethylbenzene (5.0 g, 14 mmol) and cyclopropylcarbinol (1.75 g, 24 mmol) were dissolved in THF (20 mL) under nitrogen. Triphenylphosphine (9.5 g, 36 mmol) was added and diethyl azodicarboxylate (5.7 mL, 36 mmol) dissolved in THF (10 mL) was added over 30 minutes. The reaction mixture was stirred at 20° C. for 16 hours and then concentrated in vacuo. The residue was dissolved in ethyl acetate (25 mL) and heptane (40 mL). The mixture was filtered and the filtrate was concentrated in vacuo. The residue was purified by flash chromatography (350 g silica) using heptane and ethyl acetate (9:1) as eluent to give 1.4 g of 4-cyclopropylmethoxy-1-nitro-2-trifluoromethylbenzene.

Workup

  1. additionwas added over 30 minutes
  2. concentrationconcentrated in vacuo
  3. dissolutionThe residue was dissolved in ethyl acetate (25 mL)
  4. filtrationThe mixture was filtered
  5. concentrationthe filtrate was concentrated in vacuo
  6. customThe residue was purified by flash chromatography (350 g silica)

Sources & evidence

ORD record
ord-dc2f930bc6d84044ababbd5a975317e4
Source dataset
uspto-grants-2005_04
Patent number
US06875760B2

Reaction notes

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