Potassium Iodide → 2-(4-bromophenoxy)-N-[4-chloro-3-(trifluoromethyl)phenyl]acetamide

HRID 1809153ノート

反応式

HRID 1809153 の反応式
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.Cl[CH2:10][C:11]([NH:13][C:14]1[CH:19]=[CH:18][C:17]([Cl:20])=[C:16]([C:21]([F:24])([F:23])[F:22])[CH:15]=1)=[O:12].[I-].[K+].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:10][C:11]([NH:13][C:14]2[CH:19]=[CH:18][C:17]([Cl:20])=[C:16]([C:21]([F:24])([F:22])[F:23])[CH:15]=2)=[O:12])=[CH:4][CH:3]=1

参加物

6

反応物 4

HCID 4875Potassium IodideHCID 78084-BromophenolHCID 11430Potassium CarbonateHCID 23077292-chloro-N-[4-chloro-3-(trifluoromethyl)phenyl]acetamide

生成物 1

HCID 10476772-(4-bromophenoxy)-N-[4-chloro-3-(trifluoromethyl)phenyl]acetamide収率 94.9%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

To a round bottom flask was added 4-bromophenol (1.7 g, 9.8 mmol, 1.0 eq.), acetamide 21 (2.79 g, 10.3 mmol, 1.05 eq.), potassium iodide (1.7 g, 10.3 mmol, 1.05 eq.), potassium carbonate (2.7 g, 19.6 mmol, 2.0 eq.), and acetonitrile (35.0 mL). The reaction mixture was then reluxed with vigorous stirring for 2 h. The hot reaction was then filtered to remove the insoluble potassium carbonate. The filtrate was concentrated to give 3.8 g of crude bromo-phenoxy-acetamide 22 as a light brown solid. The solid was then triturated with 10 mL of cold acetonitrile, filtered, and rinsed with 5 mL of cold acetonitrile to give pure bromo-phenoxy-acetamide 22 (1.85 g, 45% yield). Note: there was still an abundant amount of crude product in the mother liquor. LC/MSD (HP Series 1100 MSD) MS (ES+) m/z 409.9 (M+H)+1 1H-NMR, Varian 400 MHz (DMSO-d6) δ 8.20 (d, 1H), 7.90 (dd, 1H), 7.68 (d, 1H), 7.48 (d, 2H), 6.99 (d, 2H), 4.75 (s, 2H) ppm.

後処理

  1. customThe hot reaction
  2. filtrationwas then filtered
  3. customto remove the insoluble potassium carbonate
  4. concentrationThe filtrate was concentrated

出典と根拠

ORDレコード
ord-22f9b0711c3746b3aac8c1f555531886
出典データセット
uspto-grants-2013_01
特許番号
US08362017B2

反応ノート

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