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

HRID 2358757노트

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HRID 2358757 반응식
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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
85 °C

실험 절차

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%).

후처리

  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)

출처 및 근거

ORD 기록
ord-945b1e6ae39a4faea15462eb64128afc
출처 데이터셋
uspto-grants-2010_07
특허 번호
US07763731B2

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