2-Chloro-4'-fluoropropiophenone → 1-Chloro-3-(4-fluorophenyl)-5-methylhex-5-en-3-ol

HRID 1640723Notes

Reaction equation

HRID 1640723 reaction equation
[Cl:1][CH2:2][CH2:3][C:4]([C:6]1[CH:11]=[CH:10][C:9]([F:12])=[CH:8][CH:7]=1)=[O:5].I[CH2:14][C:15]([CH3:17])=[CH2:16]>C1COCC1>[Cl:1][CH2:2][CH2:3][C:4]([C:6]1[CH:7]=[CH:8][C:9]([F:12])=[CH:10][CH:11]=1)([OH:5])[CH2:16][C:15]([CH3:17])=[CH2:14]

Participants

4

Reactant 2

HCID 676722-Chloro-4'-fluoropropiophenoneHCID 108777523-Iodo-2-methylprop-1-ene

Product 1

HCID 596356741-Chloro-3-(4-fluorophenyl)-5-methylhex-5-en-3-olYield 76%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The reaction mixture was mildly exothermic, and began to reflux spontaneously. After the refluxing had ceased, the mixture was stirred for 1 h. TLC showed the 3-chloro-1-(4-fluorophenyl)propan-1-one not reacted completely. A solution of 3-iodo-2-methylprop-1-ene (18.2 g, 0.1 mol) in THF (30 mL) was added, and the mixture was stirred at rt overnight. The mixture was extracted with EtOAc (2×500 mL). The combined organic layer was dried and concentrated. The residue was purified by column chromatography on silica gel eluted with petroleum ether/EtOAc 50:1→30:1→5:1, to give 1-chloro-3-(4-fluorophenyl)-5-methylhex-5-en-3-ol (17 g, yield 76%) as an oil.

Workup

  1. temperatureto reflux spontaneously
  2. customreacted completely
  3. stirringthe mixture was stirred at rt overnight
  4. extractionThe mixture was extracted with EtOAc (2×500 mL)
  5. customThe combined organic layer was dried
  6. concentrationconcentrated
  7. customThe residue was purified by column chromatography on silica gel
  8. washeluted with petroleum ether/EtOAc 50:1→30:1→5:1

Sources & evidence

ORD record
ord-e9e494539df842109e11bb6406efcd9f
Source dataset
uspto-grants-2012_02
Patent number
US08114868B2

Reaction notes

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