Oxalyl chloride → 2,2-Difluoro-4-pentenoyl chloride

HRID 1599105

반응식

HRID 1599105 반응식
C(Cl)(=O)C([Cl:4])=O.[F:7][C:8]([F:15])([CH2:12][CH:13]=[CH2:14])[C:9](O)=[O:10]>CN(C)C=O>[F:7][C:8]([F:15])([CH2:12][CH:13]=[CH2:14])[C:9]([Cl:4])=[O:10]

참가 물질

4

반응물 2

HCID 65578Oxalyl chloride2회HCID 119546562,2-Difluoro-4-pentenoic acid

생성물 1

HCID 136650492,2-Difluoro-4-pentenoyl chloride수율 86%

시약·촉매·용매 1

HCID 6228Dimethylformamide촉매

실험 절차

Add oxalyl chloride (17.6 mL, 201.8 mmol) to compound 8c (25 g, 183.7 mmol) and dimethylformamide (3 drops) under neat conditions at room temperature. Observe gas evolution for approximately 2 h. After 5 h, treat the reaction mixture with an additional 0.08 eq of oxalyl chloride (1.2 mL) and stir for 18 h. Use fractional distillation (88°-91° C.) to obtain 24.4 g, 158 mmol of the title compound 8a as an oil in 85% yield. 19F NMR (CDCl3) δ -101.9 (t); 13C NMR (CDCl3) δ 167.3 (t, CO2H), 125.5 (s, C=C), 123.1 (s, C=C), 115.6 (t, CF2), 38.3 (t, CH2); 1H NMR (CDCl3) δ 2.90 (m, 2H), 5.33 (d, 1H), 5.36 (s, 1H), 5.74 (m, 2H).

후처리

  1. waitAfter 5 h
  2. distillationdistillation (88°-91° C.)

출처 및 근거

ORD 기록
ord-43f032b3ad1a47c582a9231c381c456a
출처 데이터셋
uspto-grants-1998_04
특허 번호
US05739354

연결된 노트

불러오는 중…