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

HRID 1497985노트

반응식

HRID 1497985 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
60 °C

실험 절차

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.

후처리

  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.

출처 및 근거

ORD 기록
ord-ba4959fc871946ae8949319b0885d9c1
출처 데이터셋
uspto-grants-2015_12
특허 번호
US09199980B2

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