Acetic Acid → Methyl 3-(((4-fluorophenyl)amino)methyl)benzoate

HRID 1497974ノート

反応式

HRID 1497974 の反応式
[CH:1]([C:3]1[CH:4]=[C:5]([CH:10]=[CH:11][CH:12]=1)[C:6]([O:8][CH3:9])=[O:7])=O.[F:13][C:14]1[CH:20]=[CH:19][C:17]([NH2:18])=[CH:16][CH:15]=1.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(Cl)Cl.O>[F:13][C:14]1[CH:20]=[CH:19][C:17]([NH:18][CH2:1][C:3]2[CH:4]=[C:5]([CH:10]=[CH:11][CH:12]=2)[C:6]([O:8][CH3:9])=[O:7])=[CH:16][CH:15]=1

参加物

7

反応物 4

HCID 176Acetic AcidHCID 97314-FluoroanilineHCID 639145Methyl 3-formylbenzoateHCID 5049666Sodium triacetoxyborohydride

生成物 1

HCID 86720703Methyl 3-(((4-fluorophenyl)amino)methyl)benzoate収率 101.9%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6344Dichloromethane溶媒2 回

実験手順

To a stirred solution of methyl 3-formylbenzoate (0.5 g, 3.046 mmol) in anhydrous DCM (15 mL) was added 4-fluoroaniline (0.303 mL, 3.198 mmol) followed by glacial acetic acid (0.174 mL, 3.046 mmol). The reaction was stirred at room temperature for 64 hours. Sodium triacetoxyborohydride (1.614 g, 7.615 mmol) was added, and the reaction was stirred at room temperature for 2 hours. Water was added to quench the reaction and the mixture was diluted with DCM. The organic layer was washed with brine, passed through a hydrophobic fit and the solvent was removed in vacuo to afford the title compound as a red oil (0.805 g, quantitative yield).

後処理

  1. stirringthe reaction was stirred at room temperature for 2 hours
  2. customto quench
  3. customthe reaction
  4. washThe organic layer was washed with brine
  5. customthe solvent was removed in vacuo

出典と根拠

ORDレコード
ord-cc69621a138541c098de318bb7fd0dc2
出典データセット
uspto-grants-2015_12
特許番号
US09199980B2

反応ノート

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