Boron trifluoride → 2-(2-Fluoro-5-nitrophenyl)propanal

HRID 30824Notes

Reaction equation

HRID 30824 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[C:11]1([CH3:14])[CH2:13][O:12]1.B(F)(F)F>C(OCC)C>[F:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[CH:11]([CH3:14])[CH:13]=[O:12]

Participants

4

Reactant 2

HCID 6356Boron trifluorideHCID 86045404HCID 86045404, compound

Product 1

HCID 866004382-(2-Fluoro-5-nitrophenyl)propanal

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

2-(2-fluoro-5-nitrophenyl)-2-methyloxirane (1 eq) was dissolved in ethyl ether (1 mL) under nitrogen. BF3-etherate (0.87 eq) was added dropwise at room temperature and after complete addition solution was allowed to stir for 1 h. Solution was then quenched with water, extracted with ethyl ether. Organics washed with brine, dried with sodium sulfate and concentrated. Crude product was purified using flash chromatography (85% Hex: 15% EtOAc) on silica to afford 2-(2-fluoro-5-nitrophenyl) propanal.

Workup

  1. customSolution was then quenched with water
  2. extractionextracted with ethyl ether
  3. washOrganics washed with brine
  4. dry with materialdried with sodium sulfate
  5. concentrationconcentrated
  6. customCrude product was purified

Sources & evidence

ORD record
ord-2d78d9fd78b64a4e9704d506f551e9ef
Source dataset
uspto-grants-2008_09
Patent number
US07423150B2

Reaction notes

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