Toluene → HCID 68957047、化合物

HRID 2191636ノート

反応式

HRID 2191636 の反応式
C1(C)C=CC=CC=1.Br[C:9]1[CH:21]=[CH:20][C:12]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])=[C:11]([N+:22]([O-:24])=[O:23])[CH:10]=1.[C:25](=[O:47])([O:31][C:32]1[CH:37]=[CH:36][CH:35]=[C:34](B2OC(C)(C)C(C)(C)O2)[CH:33]=1)[O:26][C:27]([CH3:30])([CH3:29])[CH3:28].C(=O)([O-])O.[Na+]>O.C(OCC)(=O)C.C(O)C>[C:27]([O:26][C:25]([O:31][C:32]1[CH:33]=[C:34]([C:9]2[CH:21]=[CH:20][C:12]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])=[C:11]([N+:22]([O-:24])=[O:23])[CH:10]=2)[CH:35]=[CH:36][CH:37]=1)=[O:47])([CH3:30])([CH3:28])[CH3:29]

参加物

8

反応物 4

HCID 1140TolueneHCID 516892Sodium BicarbonateHCID 27739553-(tert-Butoxycarbonyloxy)phenylboronic acid pinacol esterHCID 26369829tert-Butyl 4-bromo-2-nitrobenzoate

生成物 1

HCID 68957047HCID 68957047、化合物収率 87.3%

試薬・触媒・溶媒 3

HCID 702Ethanol溶媒HCID 962Water溶媒2 回HCID 8857Ethyl Acetate溶媒

実験手順

To toluene 24 mL solution of tert-butyl 4-bromo-2-nitrobenzoate 3.0 g were added ethanol 9.0 mL, water 4.5 mL, tert-butyl 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl carbonate 3.8 g, sodium hydrogen carbonate 2.1 g and tetrakis (triphenylphosphine)palladium(0) 0.57 g sequentially, and it was heated and refluxed under nitrogen atmosphere for 6 hours. After the reaction mixture was cooled to room temperature, ethyl acetate and water were added to it. After insoluble matter was filtrated, the organic layer was separated and collected,dried over anhydrous magnesium sulfate after washing with saturated sodium chloride aqueous solution, and the solvent was removed under reduced pressure. The obtained residue was refined by silica gel column chromatography [Fuji SILYSIA Chemical Ltd., PSQ100B(spherical type), eluent; hexane:ethyl acetate=3:1] to give tert-butyl 4-(3-(tert-butoxycarbonyl)oxyphenyl)-2-nitrobenzoate 3.6 g of yellow oil.

後処理

  1. temperatureit was heated
  2. temperaturerefluxed under nitrogen atmosphere for 6 hours
  3. filtrationAfter insoluble matter was filtrated
  4. customthe organic layer was separated
  5. washafter washing with saturated sodium chloride aqueous solution
  6. customthe solvent was removed under reduced pressure

出典と根拠

ORDレコード
ord-65915fe6e6304aeea56777715bbbc788
出典データセット
uspto-grants-2012_12
特許番号
US08327467B2

反応ノート

読み込み中…