Sodium Acetate → 3,5-Difluorotoluene

HRID 750568노트

반응식

HRID 750568 반응식
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

참가 물질

6

반응물 3

HCID 517045Sodium AcetateHCID 5188963,5-Difluorobenzyl bromideHCID 178418361HCID 178418361, 화합물

생성물 1

HCID 27783293,5-Difluorotoluene수율 98.1%

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 3283Diethyl Ether용매2회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-ea8298e511d946d481a18cd48c55e064
출처 데이터셋
uspto-grants-2008_07
특허 번호
US07405218B2

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