Nitrogen → methyl (2E)-3-[4'-(trifluoromethoxy)[1,1'-biphenyl]-4-yl]-2-propenoate

HRID 1496920

反応式

HRID 1496920 の反応式
Br[C:2]1[CH:7]=[CH:6][C:5](/[CH:8]=[CH:9]/[C:10]([O:12][CH3:13])=[O:11])=[CH:4][CH:3]=1.[F:14][C:15]([F:31])([F:30])[O:16][C:17]1[CH:22]=[CH:21][C:20](C2C=CC(O)=CC=2)=[CH:19][CH:18]=1.C([O-])([O-])=O.[K+].[K+].N#N>O1CCOCC1.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]>[F:14][C:15]([F:30])([F:31])[O:16][C:17]1[CH:22]=[CH:21][C:20]([C:2]2[CH:7]=[CH:6][C:5](/[CH:8]=[CH:9]/[C:10]([O:12][CH3:13])=[O:11])=[CH:4][CH:3]=2)=[CH:19][CH:18]=1

参加物

7

反応物 4

HCID 947NitrogenHCID 11430Potassium CarbonateHCID 816774Methyl 4-bromocinnamateHCID 120087344-(4-Trifluoromethoxyphenyl)phenol

生成物 1

HCID 54757818methyl (2E)-3-[4'-(trifluoromethoxy)[1,1'-biphenyl]-4-yl]-2-propenoate収率 85%

試薬・触媒・溶媒 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)触媒HCID 312751,4-Dioxane溶媒

実験手順

A solution of methyl (E)-3-(4-bromophenyl)-2-propenoate (99) (0.500 g, 2.07 mmol) and 4-(trifluoromethoxy)phenylboronic acid (44) (0.612 g, 2.97 mmol) in dioxane (40 mL) and aqueous K2CO3 (2M, 10 mL, 20 mmol) was purged with N2. Pd(dppf)Cl2 (0.050 g, 0.06 mmol) was added and the solution was refluxed under N2 for 1 h. The dioxane was removed and the residue was extracted with EtOAc, the organic fraction was dried and the solvent was removed. Column chromatography of the residue on silica gel using gradient elution (hexanes to CH2Cl2) gave methyl (2E)-3-[4′-(trifluoromethoxy)[1,1′-biphenyl]-4-yl]-2-propenoate (100) (0.567 g, 85%) as a white solid: mp 98-100° C.; 1H NMR (CDCl3) δ 7.73 (d, J=16.0 Hz, 1H), 7.56-7.63 (m, 6H), 7.30 (dd, J=8.8, 0.9 Hz, 2H), 6.48 (d, J=16.0 Hz, 1H), 3.82 (s, 3H). APCI MS m/z 323 [M+H]+.

後処理

  1. temperaturethe solution was refluxed under N2 for 1 h
  2. customThe dioxane was removed
  3. extractionthe residue was extracted with EtOAc
  4. customthe organic fraction was dried
  5. customthe solvent was removed
  6. washColumn chromatography of the residue on silica gel using gradient elution (hexanes to CH2Cl2)

出典と根拠

ORDレコード
ord-af23c11d57c3404a979a89cdabf7813c
出典データセット
uspto-grants-2015_12
特許番号
US09198913B2

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