5-Chloro-2-nitrobenzaldehyde → (5-Chloro-2-nitro-phenyl)-(6-chloro-pyridin-3-yl)-methanol

HRID 29500

反応式

HRID 29500 の反応式
[Cl:1][C:2]1[CH:7]=[CH:6][C:5](I)=[CH:4][N:3]=1.C([Mg]Br)(C)C.C1COCC1.[N+:19]([C:22]1[CH:29]=[CH:28][C:27]([Cl:30])=[CH:26][C:23]=1[CH:24]=[O:25])([O-:21])=[O:20]>C1COCC1>[Cl:30][C:27]1[CH:28]=[CH:29][C:22]([N+:19]([O-:21])=[O:20])=[C:23]([CH:24]([C:5]2[CH:4]=[N:3][C:2]([Cl:1])=[CH:7][CH:6]=2)[OH:25])[CH:26]=1

参加物

5

反応物 3

HCID 811235-Chloro-2-nitrobenzaldehydeHCID 43971762-Chloro-5-iodopyridineHCID 178420663HCID 178420663、化合物

生成物 1

HCID 22327314(5-Chloro-2-nitro-phenyl)-(6-chloro-pyridin-3-yl)-methanol

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-45 °C

実験手順

A solution of 1.0 g 2-chloro-5-iodopyridine (4.1 mmol, 1.0 eq.) in 10 mL anhyd. THF was stirred at −40° C. to −50° C. After five minutes, 2.2 mL of 2.1 M iPrMgBr/THF (4.6 mmol, 1.1 eq.) were added drop wise over 1 minute and the reaction mixture is maintained at −40 to −50° C. for 30 minutes. 1.3 g 2-nitro-5-chlorobenzaldehyde (7.0 mmol, 1.7 eq.) was then added and the reaction was maintained at −50° C. After 1 hour, the reaction was allowed to warm to −10° C., and quenched with 50 mL saturated brine after a further fifteen minutes. The crude product was extracted with EtOAc, dried on Na2SO4 and concentrated by rotary evaporation to yield desired product. MS: (M+H)/z=298.9

後処理

  1. temperaturethe reaction was maintained at −50° C
  2. waitAfter 1 hour
  3. temperatureto warm to −10° C.
  4. customquenched with 50 mL saturated brine after a further fifteen minutes
  5. extractionThe crude product was extracted with EtOAc
  6. customdried on Na2SO4
  7. concentrationconcentrated by rotary evaporation

出典と根拠

ORDレコード
ord-63a7bf13d186452bada32640db498840
出典データセット
uspto-grants-2008_09
特許番号
US07420055B2

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