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

HRID 1963742Notes

Reaction equation

HRID 1963742 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-9f2d8f7c17d4454c8be4c42333fa3793
Source dataset
uspto-grants-2013_04
Patent number
US08415382B2

Reaction notes

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