Potassium Carbonate → 1-Cyclopropyl-4-nitrobenzene

HRID 1898332

反応式

HRID 1898332 の反応式
[CH:1]1(B(O)O)[CH2:3][CH2:2]1.Br[C:8]1[CH:13]=[CH:12][C:11]([N+:14]([O-:16])=[O:15])=[CH:10][CH:9]=1.C(=O)([O-])[O-].[K+].[K+]>C1(C)C=CC=CC=1>[CH:1]1([C:8]2[CH:13]=[CH:12][C:11]([N+:14]([O-:16])=[O:15])=[CH:10][CH:9]=2)[CH2:3][CH2:2]1

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 114661-Bromo-4-nitrobenzeneHCID 2760897Cyclopropylboronic acid

生成物 1

HCID 3127131-Cyclopropyl-4-nitrobenzene収率 92,855.398%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

To a solution of cyclopropyl boronic acid (0.637 g, 0.00742 mmol) in dry toluene, were added 4-bromo nitrobenzene (1.00 g, 0.00495 mmol) and tetrakis triphenylphosphine palladium (0.099 g, 0.0099 mol). Degassed the reaction mixture for 30 minutes then added potassium carbonate (1.36 g, 0.009 mmol). The reaction mass was refluxed for 48 h. The excess of solvent was removed under vacuum and the reaction mass was diluted with water and extracted with ethyl acetate. The organic layer was separated, dried over anhydrous sodium sulphate and concentrated. The obtained crude was purified by column chromatography on silica gel eluting with 4% DCM: MeOH to afford 0.750 g of the desired product. 1HNMR (DMSO-d6): δ 0.82-0.84 (m, 2H), 1.09-1.13 (m, 2H), 2.01 (m, 1H), 7.32 (d, J=8.7 Hz, 2H), 8.09 (d, J=8.7 Hz, 2H).

後処理

  1. customDegassed the reaction mixture for 30 minutes
  2. temperatureThe reaction mass was refluxed for 48 h
  3. customThe excess of solvent was removed under vacuum
  4. additionthe reaction mass was diluted with water
  5. extractionextracted with ethyl acetate
  6. customThe organic layer was separated
  7. dry with materialdried over anhydrous sodium sulphate
  8. concentrationconcentrated
  9. customThe obtained crude
  10. customwas purified by column chromatography on silica gel eluting with 4% DCM

出典と根拠

ORDレコード
ord-a321db58508d46919714678f2ca072d6
出典データセット
uspto-grants-2013_08
特許番号
US08519149B2

関連ノート

読み込み中…