Sodium Acetate → 3,5-Difluorotoluene

HRID 750568ノート

反応式

HRID 750568 の反応式
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+].[H][H]>CCOCC.[Pd]>[F:9][C:7]1[CH:8]=[C:3]([CH3:2])[CH:4]=[C:5]([F:10])[CH:6]=1

参加物

6

反応物 3

HCID 517045Sodium AcetateHCID 5188963,5-Difluorobenzyl bromideHCID 178418361HCID 178418361、化合物

生成物 1

HCID 27783293,5-Difluorotoluene収率 98.1%

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 3283Diethyl Ether溶媒2 回

実験手順

A mixture of 1-bromomethyl-3,5-difluoro-benzene (75 g, 0.362 mol), Pd/C (5%, 5 g), and sodium acetate (208 g, 2.54 mol) in ether (300 mL) was treated with hydrogen gas (50 psi) in a Parr shaker for 2 days. The mixture was filtered through Celite and the organic solution washed three times with saturated aqueous sodium bicarbonate solution. The aqueous layers were washed with ether and the combined organic layers dried (MgSO4), filtered, and partially concentrated by evaporation using a cold water bath. The volatile product was obtained as a mixture with ether and the ratio (˜3:2, ether:product, g:g) calculated based on 1H NMR integration to determine actual yield (45.5 g, 0.355 mol, 98%) of product for scaling reagents in the ensuing reaction. 1H NMR (400 MHz, CDCl3) δ 2.25 (s, 3H), 6.51-6.56 (m, 1H), 6.58-6.60 (m, 2H) ppm.

後処理

  1. filtrationThe mixture was filtered through Celite
  2. washthe organic solution washed three times with saturated aqueous sodium bicarbonate solution
  3. washThe aqueous layers were washed with ether
  4. dry with materialthe combined organic layers dried (MgSO4)
  5. filtrationfiltered
  6. concentrationpartially concentrated by evaporation
  7. customThe volatile product was obtained as a mixture with ether

出典と根拠

ORDレコード
ord-ea8298e511d946d481a18cd48c55e064
出典データセット
uspto-grants-2008_07
特許番号
US07405218B2

反応ノート

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