Sodium Carbonate → Tert-butyl 2-(benzamido)-4-(4-hydroxyphenyl)benzoate

HRID 1673468ノート

反応式

HRID 1673468 の反応式
[OH:1][C:2]1[CH:7]=[CH:6][C:5](B(O)O)=[CH:4][CH:3]=1.C(=O)([O-])[O-].[Na+].[Na+].[C:17]([NH:25][C:26]1[CH:38]=[C:37](Br)[CH:36]=[CH:35][C:27]=1[C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])(=[O:24])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>CN(C)C(=O)C>[C:17]([NH:25][C:26]1[CH:38]=[C:37]([C:5]2[CH:6]=[CH:7][C:2]([OH:1])=[CH:3][CH:4]=2)[CH:36]=[CH:35][C:27]=1[C:28]([O:30][C:31]([CH3:33])([CH3:34])[CH3:32])=[O:29])(=[O:24])[C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

参加物

5

反応物 3

HCID 10340Sodium CarbonateHCID 27343604-Hydroxyphenylboronic acidHCID 67343005Tert-butyl 2-(benzamido)-4-bromobenzoate

生成物 1

HCID 67343868Tert-butyl 2-(benzamido)-4-(4-hydroxyphenyl)benzoate

試薬・触媒・溶媒 1

HCID 31374Dimethylacetamide溶媒

反応条件

温度
110 °C

実験手順

39 mg of 4-hydroxyphenylboronic acid, 49 mg of sodium carbonate and 6 mg of polymer supported bis(acetato)triphenylphosphine palladium(II) were added to 2.5 mL of N,N-dimethylacetamide solution containing 70 mg of tert-butyl 2-(benzamido)-4-bromobenzoate, and stirred at 110° C. for 20 hours. After the reaction mixture was cooled to room temperature, 6 mg of polymer supported bis(acetato)triphenylphosphine palladium(II) was added and stirred at 110° C. for 22 hours. After the reaction mixture was cooled to room temperature, insoluble were removed by filtration and ethyl acetate and 10% citric acid, aqueous solution were added. The organic layer was separated and dried over anhydrous magnesium sulfate after washed with 10% citric acid aqueous solution and a saturated sodium chloride aqueous solution sequentially, and the solvent was evaporated under reduced pressure. The obtained residue was purified with silica gel column chromatography [Flash Tube 2008 manufactured by Trikonex company, eluent; hexane: ethyl acetate=2:1] to obtain tert-butyl 2-(benzamido)-4-(4-hydroxyphenyl)benzoate.

後処理

  1. temperatureAfter the reaction mixture was cooled to room temperature
  2. additionwas added
  3. stirringstirred at 110° C. for 22 hours
  4. temperatureAfter the reaction mixture was cooled to room temperature
  5. custominsoluble were removed by filtration and ethyl acetate and 10% citric acid, aqueous solution
  6. additionwere added
  7. customThe organic layer was separated
  8. dry with materialdried over anhydrous magnesium sulfate
  9. washafter washed with 10% citric acid aqueous solution
  10. customa saturated sodium chloride aqueous solution sequentially, and the solvent was evaporated under reduced pressure
  11. customThe obtained residue was purified with silica gel column chromatography [Flash Tube 2008 manufactured by Trikonex company, eluent; hexane: ethyl acetate=2:1]

出典と根拠

ORDレコード
ord-de347bb0d721454683df4863c6674b84
出典データセット
uspto-grants-2011_08
特許番号
US07999132B2

反応ノート

読み込み中…