3-Hydroxybenzaldehyde → 3-(4-Chloro-2-nitro-phenoxy)-benzaldehyde

HRID 2197921ノート

反応式

HRID 2197921 の反応式
Br[C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10].[OH:12][C:13]1[CH:14]=[C:15]([CH:18]=[CH:19][CH:20]=1)[CH:16]=[O:17].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[Cl:8][C:5]1[CH:6]=[CH:7][C:2]([O:12][C:13]2[CH:14]=[C:15]([CH:18]=[CH:19][CH:20]=2)[CH:16]=[O:17])=[C:3]([N+:9]([O-:11])=[O:10])[CH:4]=1

参加物

5

反応物 3

HCID 1013-HydroxybenzaldehydeHCID 11430Potassium CarbonateHCID 27949042-Bromo-5-chloronitrobenzene

生成物 1

HCID 92813413-(4-Chloro-2-nitro-phenoxy)-benzaldehyde収率 41%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
85 °C

実験手順

To a solution of DMF (50 mL) was added 1-bromo-2-nitro-4-chloro-benzene (10.0 g, 42.2 mmol), 3-hydroxybenzaldehyde (5.2 g, 42.2 mmol), and K2CO3 (11.5 g, 84.6 mmol). The solution was heated to 85° C. and stirred overnight. The reaction was poured into distill water and extracted with ethyl acetate. The combined organic layers were washed with distilled water, brine, and dried over Na2SO4, filtered and concentrated under vacuum giving the crude title compound. This solid was purified by silica gel column chromatography eluting with hexanes/ethyl acetate (4:1) to give the title compound (4.4 gm, 41%).

後処理

  1. additionThe reaction was poured
  2. distillationinto distill water
  3. extractionextracted with ethyl acetate
  4. washThe combined organic layers were washed with distilled water, brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under vacuum
  8. customgiving the crude title compound
  9. customThis solid was purified by silica gel column chromatography
  10. washeluting with hexanes/ethyl acetate (4:1)

出典と根拠

ORDレコード
ord-ac4c381a28564f6c81080513ace2b1f2
出典データセット
uspto-grants-2012_12
特許番号
US08338605B2

反応ノート

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