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

HRID 713828ノート

反応式

HRID 713828 の反応式
[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

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
0 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-d3a23dc1964142ba9934d2e2e47a4b82
出典データセット
uspto-grants-2015_11
特許番号
US09186424B2

反応ノート

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