Sodium Acetate → 3,5-Difluorotoluene

HRID 1894707Notes

Reaction equation

HRID 1894707 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 then 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-1e3e4144fb9f4486bdf3062d7aa99c55
Source dataset
uspto-grants-2013_08
Patent number
US08513289B2

Reaction notes

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