Bromide ion → HCID 60098017, compound

HRID 30822Notes

Reaction equation

HRID 30822 reaction equation
[CH3:1][Si]([N-][Si](C)(C)C)(C)C.[K+].[Br-].[F:12][C:13]1[CH:18]=[CH:17][C:16]([N+:19]([O-:21])=[O:20])=[CH:15][C:14]=1[C:22](=O)[CH3:23]>C1(C)C=CC=CC=1.C1COCC1>[F:12][C:13]1[CH:18]=[CH:17][C:16]([N+:19]([O-:21])=[O:20])=[CH:15][C:14]=1[C:22]([CH3:23])=[CH2:1]

Participants

6

Reactant 3

HCID 259Bromide ionHCID 27810671-(2-Fluoro-5-nitrophenyl)ethan-1-oneHCID 3251421Potassium bis(trimethylsilyl)amide

Product 1

HCID 60098017HCID 60098017, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

KHMDS(1 eq) in toluene is added dropwise over 5 minutes to a stirred suspension of triphenylphosphinemethyl bromide(1.2 eq) in THF at −78° C. under nitrogen. After complete addition solution is allowed to warm to room temperature for 5 minutes then cooled a second time to −78° C. 1-(2-fluoro-5-nitrophenyl)ethanone(1 eq) in THF is then added via cannulla into the cold suspension over 10 minutes. Resulting mixture is then allowed to warm to room temperature and stirred for 1 h. Solvent is then removed under reduced pressure, cyclohexane is then added and mixture heated briefly to reflux, cooled to room temperature, filtered and filtrate concentrated. Crude product is purified using flash chromatography(85% Hex:15% EtoAc) on silica to afford 1-fluoro-4-nitro-2-(prop-1-en-2-yl)benzene.

Workup

  1. temperaturethen cooled a second time to −78° C
  2. customResulting mixture
  3. temperatureto warm to room temperature
  4. customSolvent is then removed under reduced pressure, cyclohexane
  5. additionis then added
  6. temperaturemixture heated briefly
  7. temperatureto reflux
  8. temperaturecooled to room temperature
  9. filtrationfiltered
  10. concentrationfiltrate concentrated
  11. customCrude product is purified

Sources & evidence

ORD record
ord-13fedae8b1144a07907cc79ec7325282
Source dataset
uspto-grants-2008_09
Patent number
US07423150B2

Reaction notes

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