Pentanal → 1-(3,5-Difluorophenyl)pentan-1-ol

HRID 466493Notes

Reaction equation

HRID 466493 reaction equation
[CH:1](=[O:6])[CH2:2][CH2:3][CH2:4][CH3:5].Br[C:8]1[CH:13]=[C:12]([F:14])[CH:11]=[C:10]([F:15])[CH:9]=1.[Mg].[Cl-].[NH4+]>CCOCC.C1COCC1>[F:15][C:10]1[CH:9]=[C:8]([CH:1]([OH:6])[CH2:2][CH2:3][CH2:4][CH3:5])[CH:13]=[C:12]([F:14])[CH:11]=1

Participants

7

Reactant 4

HCID 8063PentanalHCID 25517Ammonium ChlorideHCID 1363131-Bromo-3,5-difluorobenzeneHCID 5462224Magnesium

Product 1

HCID 225984431-(3,5-Difluorophenyl)pentan-1-olYield 116%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of pentanal (19.0 g, 0.22 mol) in dry ether (75 ml) was added dropwise to a stirred solution of the Grignard reagent at room temperature, under dry nitrogen, prepared from 1-bromo-3,5-difluorobenzene (50.2 g, 0.26 mol) and magnesium (7.25 g, 0.30 mol) in dry THF (100 ml). The stirred mixture was heated under reflux for 2 h, cooled and a saturated solution of ammonium chloride (300 ml) was added. The product was extracted into ether (twice), and the combined ethereal extracts were washed with water and dried (MgSO4). The solvent was removed in vacuo to give a pale-orange liquid (51.1 g) which was distilled to yield a colourless liquid. Smaller quantities of crude product were purified by column chromatography (silca gel/dichloromethane) to yield a colourless liquid (92%).

Workup

  1. temperatureThe stirred mixture was heated
  2. temperatureunder reflux for 2 h
  3. temperaturecooled
  4. extractionThe product was extracted into ether (twice), and the combined ethereal extracts
  5. washwere washed with water
  6. dry with materialdried (MgSO4)
  7. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-1af95d80c1ec4785aeff7d0024730c01
Source dataset
uspto-grants-1992_10
Patent number
US05156763

Reaction notes

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