Triethylamine → Methyl 3-(2-bromo-3,5-difluorophenyl)propanoate

HRID 625696

반응식

HRID 625696 반응식
Br[C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[C:4]([F:9])[C:3]=1[Br:10].[CH3:11][O:12][CH:13]([O:16]C)[CH:14]=[CH2:15].C(N(CC)CC)C>[Cl-].C([N+](CCCC)(CCCC)CCCC)CCC.CN(C)C=O>[Br:10][C:3]1[C:4]([F:9])=[CH:5][C:6]([F:8])=[CH:7][C:2]=1[CH2:15][CH2:14][C:13]([O:12][CH3:11])=[O:16]

참가 물질

6

반응물 3

HCID 8471TriethylamineHCID 80145Acrolein dimethyl acetalHCID 27245171,2-Dibromo-3,5-difluorobenzene

생성물 1

HCID 89826041Methyl 3-(2-bromo-3,5-difluorophenyl)propanoate

시약·촉매·용매 2

HCID 70681Tetrabutylammonium Chloride촉매HCID 6228Dimethylformamide용매

반응 조건

온도
90 °C

실험 절차

A mixture of 1,2-dibromo-3,5-difluorobenzene (4.5 g), 3,3-dimethoxyprop-1-ene (5.1 mL), tetrabutylammonium chloride (4.6 g) and triethylamine (3.5 mL) in N,N-dimethylformamide (50 mL) is purged with nitrogen for 20 minutes. Palladium-(II)-acetate (111 mg) is added and the mixture heated for 16 hours at 90° C. After cooling the mixture is partitioned between aqueous HCl (1 M) and diethyl ether, the organic layer dried (Na2SO4), volatiles evaporated under reduced pressure and the residue purified by column chromatography (silica gel; hexane:ethyl acetate 98:2→80:20) to give the title compound (Yield 3.6 g).

후처리

  1. customis purged with nitrogen for 20 minutes
  2. additionPalladium-(II)-acetate (111 mg) is added
  3. temperatureAfter cooling the mixture
  4. customis partitioned between aqueous HCl (1 M) and diethyl ether
  5. dry with materialthe organic layer dried (Na2SO4)
  6. customvolatiles evaporated under reduced pressure
  7. customthe residue purified by column chromatography (silica gel; hexane:ethyl acetate 98:2→80:20)

출처 및 근거

ORD 기록
ord-8f53b8bc5e954936a05f94d1a5e40149
출처 데이터셋
uspto-grants-2016_04
특허 번호
US09308194B2

연결된 노트

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