Potassium Carbonate → 2-(3-Bromo-5-methylphenoxy)-5-(trifluoromethyl)pyridine

HRID 1666452ノート

反応式

HRID 1666452 の反応式
[Br:1][C:2]1[CH:3]=[C:4]([OH:9])[CH:5]=[C:6]([CH3:8])[CH:7]=1.C([O-])([O-])=O.[K+].[K+].Cl[C:17]1[CH:22]=[CH:21][C:20]([C:23]([F:26])([F:25])[F:24])=[CH:19][N:18]=1>CN(C=O)C>[Br:1][C:2]1[CH:3]=[C:4]([CH:5]=[C:6]([CH3:8])[CH:7]=1)[O:9][C:17]1[CH:22]=[CH:21][C:20]([C:23]([F:26])([F:25])[F:24])=[CH:19][N:18]=1

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 923422-Chloro-5-(trifluoromethyl)pyridineHCID 126484093-Bromo-5-methylphenol

生成物 1

HCID 668769062-(3-Bromo-5-methylphenoxy)-5-(trifluoromethyl)pyridine収率 85.2%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
110 °C

実験手順

To a solution of 3-bromo-5-methylphenol (2.0 g, 0.0106 mol) in DMF (15 mL) was added K2CO3 (2.93 g, 0.02 mol) at RT. 2-Chloro-5-(trifluoromethyl)pyridine (1.94 g, 0.0106 mol) was added and the reaction was refluxed at 110° C. for 12 h. The reaction mixture was quenched with water and extracted with EtOAc three times. The total organic extract was washed with water and brine, dried over sodium sulfate and concentrated under reduced pressure to give the title compound (3 g, 84.5%). 1H NMR (500 MHz, CDCl3): δ 8.45 (s, 1H), 7.92 (d, J=8.6 Hz, 1H), 7.26 (d, J=14.95 Hz, 1H), 7.13 (s, 1H), 7.03 (d, J=10 Hz, 1H), 6.90 (s, 1H), 2.36 (s, 3H).

後処理

  1. customThe reaction mixture was quenched with water
  2. extractionextracted with EtOAc three times
  3. extractionThe total organic extract
  4. washwas washed with water and brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-026251bf2d3c480580b3d6a5c473e5ca
出典データセット
uspto-grants-2011_10
特許番号
US08044052B2

反応ノート

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