2-Fluoroaniline → Methyl 2-fluoro-4-[(2-fluoroanilino)methyl]benzoate

HRID 1497985ノート

反応式

HRID 1497985 の反応式
[F:1][C:2]1[CH:8]=[CH:7][CH:6]=[CH:5][C:3]=1[NH2:4].C(=O)([O-])[O-].[K+].[K+].Br[CH2:16][C:17]1[CH:26]=[CH:25][C:20]([C:21]([O:23][CH3:24])=[O:22])=[C:19]([F:27])[CH:18]=1>CN(C=O)C>[F:27][C:19]1[CH:18]=[C:17]([CH2:16][NH:4][C:3]2[CH:5]=[CH:6][CH:7]=[CH:8][C:2]=2[F:1])[CH:26]=[CH:25][C:20]=1[C:21]([O:23][CH3:24])=[O:22]

参加物

5

反応物 3

HCID 95842-FluoroanilineHCID 11430Potassium CarbonateHCID 18759821methyl 4-(bromomethyl)-2-fluorobenzoate

生成物 1

HCID 86720707Methyl 2-fluoro-4-[(2-fluoroanilino)methyl]benzoate

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
60 °C

実験手順

To a mixture of 2-fluoroaniline (0.12 mL, 1.2 mmol) and potassium carbonate (207 mg, 1.5 mL) in DMF (5 mL) was added methyl 4-(bromomethyl)-2-fluoro-benzoate (247 mg, 1 mmol). The mixture was heated to 60° C. for 18 hours. The solvent was removed in vacuo. The mixture was partitioned between DCM (15 mL) and water (15 mL), the layers were separated and the organic phase was passed through a hydrophobic fit. The solvent was removed in vacuo and the residue was used directly in the next step without any further purification. LCMS (Method 2): [MH+]=278 at 3.60 min.

後処理

  1. customThe solvent was removed in vacuo
  2. customThe mixture was partitioned between DCM (15 mL) and water (15 mL)
  3. customthe layers were separated
  4. customThe solvent was removed in vacuo
  5. customthe residue was used directly in the next step without any further purification
  6. customat 3.60 min.

出典と根拠

ORDレコード
ord-ba4959fc871946ae8949319b0885d9c1
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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