Sodium Acetate → 3,5-Difluorotoluene

HRID 908241Notes

Reaction equation

HRID 908241 reaction equation
Br[CH2:2][C:3]1[CH:8]=[C:7]([F:9])[CH:6]=[C:5]([F:10])[CH:4]=1.C([O-])(=O)C.[Na+]>CCOCC.[Pd]>[F:9][C:7]1[CH:8]=[C:3]([CH3:2])[CH:4]=[C:5]([F:10])[CH:6]=1

Participants

5

Reactant 2

HCID 517045Sodium AcetateHCID 5188963,5-Difluorobenzyl bromide

Product 1

HCID 27783293,5-Difluorotoluene

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 3283Diethyl EtherSolvent

Procedure

A mixture of 1-(bromomethyl)-3,5-difluorobenzene (50 g, 0.24 mol), 10% Pd/C (3 g) and sodium acetate (140 g, 1.7 mol) in anhydrous ether (250 mL) was stirred under hydrogen at atmospheric pressure for 24 hr. The mixture was filtered and the filtrate was dried over anhydrous Na2SO4, filtered and used directly in the next step. 1H-NMR (500 MHz, CDCl3): δ 6.56 (d, 2H, J=6.0 Hz), 6.47 (t, 1H, J=9.0 Hz), 2.22 (s, 3H).

Workup

  1. filtrationThe mixture was filtered
  2. dry with materialthe filtrate was dried over anhydrous Na2SO4
  3. filtrationfiltered

Sources & evidence

ORD record
ord-142d52581a6f4ee5a4b9467cfba32377
Source dataset
uspto-grants-2011_09
Patent number
US08017605B2

Reaction notes

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