Fluoroacetyl chloride → N-(2,2,-Dimethyl-2,3-dihydrobenzofuran-7-ylmethyl)-2-Fluoro-N-(2-phenoxy phenyl)acetamide

HRID 1618809노트

반응식

HRID 1618809 반응식
[CH3:1][C:2]1([CH3:26])[CH2:6][C:5]2[CH:7]=[CH:8][CH:9]=[C:10]([CH2:11][NH:12][C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[O:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[C:4]=2[O:3]1.[F:27][CH2:28][C:29](Cl)=[O:30]>C(Cl)Cl>[CH3:1][C:2]1([CH3:26])[CH2:6][C:5]2[CH:7]=[CH:8][CH:9]=[C:10]([CH2:11][N:12]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[O:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[C:29](=[O:30])[CH2:28][F:27])[C:4]=2[O:3]1

참가 물질

4

반응물 2

HCID 9663Fluoroacetyl chlorideHCID 67257445N-(2,2,-Dimethyl-2,3-dihydrobenzofuran-7-ylmethyl)-N-(2-phenoxy phenyl)amine

생성물 1

HCID 67258041N-(2,2,-Dimethyl-2,3-dihydrobenzofuran-7-ylmethyl)-2-Fluoro-N-(2-phenoxy phenyl)acetamide수율 72.3%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

반응 조건

온도
0 °C

실험 절차

To a solution of N-(2,2,-Dimethyl-2,3-dihydrobenzofuran-7-ylmethyl)-N-(2-phenoxy phenyl)amine (0.20 g, 0.58 mmol) dissolved in DCM (2 mL) was added TEA (0.24 g, 2.32 mmol, 0.32 mL). The reaction was cooled to 0° C. and fluoroacetyl chloride (0.11 g, 1.16 mmol, 0.08 mL) was added. The mixture was stirred at room temperature for 1 h. The solvents were removed in vacuo, the residue quenched with water (10 mL), extracted with DCM (2×20 mL), dried over MgSO4, filtered and solvents removed in vacuo. The crude material was purified by silica gel chromatography eluting with DCM (A) and MeOH (B) (1% B, 80 g, 2 CV, 60 mL/min) to afford 170 mg (72%) of N-(2,2,-Dimethyl-2,3-dihydrobenzofuran-7-ylmethyl)-2-Fluoro-N-(2-phenoxy phenyl)acetamide as a pale yellow oil.

후처리

  1. customThe solvents were removed in vacuo
  2. customthe residue quenched with water (10 mL)
  3. extractionextracted with DCM (2×20 mL)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customsolvents removed in vacuo
  7. customThe crude material was purified by silica gel chromatography
  8. washeluting with DCM (A) and MeOH (B) (1% B, 80 g, 2 CV, 60 mL/min)

출처 및 근거

ORD 기록
ord-78d836517bc440c596520f27b8943d8a
출처 데이터셋
uspto-grants-2014_07
특허 번호
US08771641B2

반응 노트

불러오는 중…