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

HRID 1741551Notes

Reaction equation

HRID 1741551 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 (silica 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-b7dee7ff80284a43b6cf00918591f552
Source dataset
uspto-grants-1994_08
Patent number
US05334327

Reaction notes

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