Iodine → 2,2-Difluoro-4-pentenoic acid

HRID 329818

반응식

HRID 329818 반응식
Cl[C:2]([F:10])([F:9])[C:3]([O:5]CC=C)=[O:4].[CH3:11][Si](C)(C)Cl.II.[C:18](#N)[CH3:19]>[Zn]>[F:10][C:2]([F:9])([CH2:11][CH:18]=[CH2:19])[C:3]([OH:5])=[O:4]

참가 물질

6

반응물 4

HCID 807IodineHCID 6342AcetonitrileHCID 6397ChlorotrimethylsilaneHCID 10012339Allyl chlorodifluoroacetate

생성물 1

HCID 119546562,2-Difluoro-4-pentenoic acid

시약·촉매·용매 1

HCID 23994Zinc촉매

반응 조건

온도
100 °C

실험 절차

100.0 g (0.59 mol) of allyl chlorodifluoroacetate, 42.2 g (0.65 mol) of zinc dust (activated according to Fieser & Fieser), 96.7 g (0.88 mol) of trimethylchlorosilane and 400 ml of absolute acetonitrile are introduced together into a glass autoclave, a spatula tip of iodine is added and the mixture is heated for 48 hours at 100° C. The zinc salt which has precipitated is filtered off, the filtrate is hydrolysed with H2O and rendered basic with 2N NaOH. The dark brown aqueous phase, extracted with pentane, is acidified with half-concentrated HCl, and the product is extracted with ethyl acetate. After the organic phase has been dried over MgSO4 and evaporated in a rotary evaporator (RE), the residue is distilled in vacuo. Yield: 59.4 g (74%) of a colourless oil of boiling point 73°-75° C./15.6 mbar.

후처리

  1. customThe zinc salt which has precipitated
  2. filtrationis filtered off
  3. extractionThe dark brown aqueous phase, extracted with pentane
  4. extractionthe product is extracted with ethyl acetate
  5. dry with materialAfter the organic phase has been dried over MgSO4
  6. customevaporated in a rotary evaporator (RE), the residue
  7. distillationis distilled in vacuo

출처 및 근거

ORD 기록
ord-3b5bd5bdad2344b08f05f11c901ccccb
출처 데이터셋
uspto-grants-1990_01
특허 번호
US04892962

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