Water → 1-Chloro-4-methoxy-5-nitro-2-vinylbenzene

HRID 1019763노트

반응식

HRID 1019763 반응식
Br[C:2]1[CH:7]=[C:6](F)[C:5]([N+:9]([O-:11])=[O:10])=[CH:4][C:3]=1[Cl:12].C(Cl)Cl.C(N([CH2:21][CH3:22])CC)C.O.[CH2:24]([OH:27])CC>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[Cl:12][C:3]1[CH:4]=[C:5]([N+:9]([O-:11])=[O:10])[C:6]([O:27][CH3:24])=[CH:7][C:2]=1[CH:21]=[CH2:22]

참가 물질

7

반응물 5

HCID 962WaterHCID 10311-PropanolHCID 6344DichloromethaneHCID 8471TriethylamineHCID 104001051-Bromo-2-chloro-5-fluoro-4-nitrobenzene

생성물 1

HCID 674659471-Chloro-4-methoxy-5-nitro-2-vinylbenzene수율 75%

시약·촉매·용매 1

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)촉매

실험 절차

A mixture of 1-bromo-2-chloro-5-fluoro-4-nitrobenzene (13.0 g, 49.24 mmol), PdCl2(dppf).DCM (0.804 g, 0.98 mmol), potassium ethenyl(trifluoro)borate (7.88 g, 59.09 mmol) and triethylamine (6.87 mL, 49.24 mmol) in n-propanol (130 mL) was heated to reflux for 4 hours. The mixture was allowed to cool to room temperature and poured into water (500 mL). The mixture was extracted with DCM (2×300 mL) then the combined organic extracts were dried (Na2SO4) and the solvent removed under reduced pressure. The residue was purified by column chromatography on neutral silica gel using 1-2% ethyl acetate in hexane to give the title compound (7.8 g, 75%) as a white solid.

후처리

  1. temperatureto reflux for 4 hours
  2. extractionThe mixture was extracted with DCM (2×300 mL)
  3. dry with materialthe combined organic extracts were dried (Na2SO4)
  4. customthe solvent removed under reduced pressure
  5. customThe residue was purified by column chromatography on neutral silica gel using 1-2% ethyl acetate in hexane

출처 및 근거

ORD 기록
ord-0bc8fa9a29274ad99cf421727c93e236
출처 데이터셋
uspto-grants-2014_05
특허 번호
US08716287B2

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