4-Fluoroaniline → Picolinafen

HRID 650236ノート

反応式

HRID 650236 の反応式
Cl[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([O:8][C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([C:15]([F:18])([F:17])[F:16])[CH:10]=2)[N:3]=1.[F:19][C:20]1[CH:26]=[CH:25][C:23]([NH2:24])=[CH:22][CH:21]=1.[C:27](=O)([O-])[O-:28].[Na+].[Na+].COC1C=CC(P(C2C=CC(OC)=CC=2)C2C=CC(OC)=CC=2)=CC=1>CC1CCCCC1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[F:19][C:20]1[CH:26]=[CH:25][C:23]([NH:24][C:27]([C:2]2[CH:7]=[CH:6][CH:5]=[C:4]([O:8][C:9]3[CH:14]=[CH:13][CH:12]=[C:11]([C:15]([F:18])([F:17])[F:16])[CH:10]=3)[N:3]=2)=[O:28])=[CH:22][CH:21]=1

参加物

7

反応物 4

HCID 97314-FluoroanilineHCID 10340Sodium CarbonateHCID 70071Phosphine, tris(4-methoxyphenyl)-HCID 110111722-Chloro-6-[3-(trifluoromethyl)phenoxy]pyridine

生成物 1

HCID 3294375Picolinafen

試薬・触媒・溶媒 2

HCID 167845palladium(II) acetate触媒HCID 7962Methylcyclohexane溶媒2 回

反応条件

温度
80 °C

実験手順

Analogously to Example 4, 6.84 g (25 mmol) of 2-chloro-6-[3-(trifluoromethyl)phenoxy]pyridine, 3.33 g (30 mmol) of 4-fluoroaniline, 2.92 g (27.5 mmol) of sodium carbonate, 5.6 mg (25 μmol) of palladium(II) acetate and 260 mg (0.75 mmol) of tris(4-methoxyphenyl)phosphine in 25 ml of methylcyclohexane were reacted under a CO pressure of 7.5 bar for 20 hours. After cooling to 80° C., the reaction mixture was diluted with 65 ml of warm methylcyclohexane. The salts were filtered off and washed with 10 ml of warm methylcyclohexane. On cooling to 5° C. the product crystallized. The yield was 8.1 g (86 percent) of a light beige solid. The melting point was 104.5° to 105.1° C.

後処理

  1. filtrationThe salts were filtered off
  2. washwashed with 10 ml of warm methylcyclohexane
  3. temperatureOn cooling to 5° C. the product
  4. customcrystallized

出典と根拠

ORDレコード
ord-16662f582fef43ff9c8839a9a1b97838
出典データセット
uspto-grants-2001_08
特許番号
US06271372B1

反応ノート

読み込み中…