Water → 3-(4-Fluorophenyl)propan-1-ol

HRID 2364124Notes

Reaction equation

HRID 2364124 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5](I)=[CH:4][CH:3]=1.C([O-])(O)=O.[Na+].[CH2:14]([OH:17])[CH:15]=[CH2:16].O>[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1.CN(C=O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.CCOCC>[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:16][CH2:15][CH2:14][OH:17])=[CH:4][CH:3]=1

Participants

9

Reactant 4

HCID 962WaterHCID 7858Allyl AlcoholHCID 96054-FluoroiodobenzeneHCID 516892Sodium Bicarbonate

Product 1

HCID 137472413-(4-Fluorophenyl)propan-1-ol

Reagents, catalysts & solvents 4

HCID 66133Benzyl triethylammonium chlorideCatalystHCID 167845palladium(II) acetateCatalystHCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

To a mixture of 1-fluoro-4-iodobenzene (300 g, 1.35 mol), benzyltriethylammonium chloride (300 g, 1.35 mol), NaHCO3 (283 g, 3.4 mol) and allyl alcohol (138 mL, 2.0 mol) in DMF (300 mL) was added palladium acetate (3.0 g, 13.5 mmol). The mixture was heated at 50° C. for 5 h with stirring. Water (1 L) and Et2O (1 L) were added at rt. After filtration through Celite, the filtrate was extracted with Et2O. The extracts were washed with H2O and brine, then dried and concentrated to yield the product: 1H NMR (CDCl3) δ 9.81 (1H, s), 7.16 (2H, m), 6.97 (2H, m), 2.93 (2H, t, J=7.5 Hz), 2.77 (2H, t, J=7.5 Hz).

Workup

  1. filtrationAfter filtration through Celite
  2. extractionthe filtrate was extracted with Et2O
  3. washThe extracts were washed with H2O and brine
  4. customdried
  5. concentrationconcentrated
  6. customto yield the product

Sources & evidence

ORD record
ord-099379ec35ef42599b55f192346e1ead
Source dataset
uspto-grants-2014_04
Patent number
US08691991B2

Reaction notes

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