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

HRID 1019763ノート

反応式

HRID 1019763 の反応式
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]

参加物

7

反応物 5

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

生成物 1

HCID 674659471-Chloro-4-methoxy-5-nitro-2-vinylbenzene収率 75%

試薬・触媒・溶媒 1

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

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-0bc8fa9a29274ad99cf421727c93e236
出典データセット
uspto-grants-2014_05
特許番号
US08716287B2

反応ノート

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