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Ethanol → 4-(6-Cyano-2-naphthyloxy)-3-(2-formylphenyl)nitrobenzene

HRID 895713
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HRID 895713 반응식
Br[C:2]1[CH:3]=[C:4]([N+:21]([O-:23])=[O:22])[CH:5]=[CH:6][C:7]=1[O:8][C:9]1[CH:18]=[CH:17][C:16]2[C:11](=[CH:12][CH:13]=[C:14]([C:19]#[N:20])[CH:15]=2)[CH:10]=1.[CH:24]([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=1B(O)O)=[O:25].C1(C)C=CC=CC=1.C(O)C>C(=O)([O-])[O-].[Na+].[Na+].C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O>[C:19]([C:14]1[CH:15]=[C:16]2[C:11](=[CH:12][CH:13]=1)[CH:10]=[C:9]([O:8][C:7]1[CH:6]=[CH:5][C:4]([N+:21]([O-:23])=[O:22])=[CH:3][C:2]=1[C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][C:26]=1[CH:24]=[O:25])[CH:18]=[CH:17]2)#[N:20]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

8

반응물 4

HCID 702EthanolHCID 1140TolueneHCID 2921892-Formylphenylboronic acidHCID 223809233-Bromo-4-(6-cyano-2-naphthyloxy)nitrobenzene

생성물 1

HCID 223809674-(6-Cyano-2-naphthyloxy)-3-(2-formylphenyl)nitrobenzene

시약·촉매·용매 3

HCID 178418397
HCID 178418397, 화합물
촉매
HCID 962Water용매
HCID 10340Sodium Carbonate용매

실험 절차

The compound (3-bromo-4-(6-cyano-2-naphthyloxy)nitrobenzene) (1 g) obtained in a previous production example, 2-formylphenyl boronic acid (610 mg) and tetrakis(triphenylphosphine)palladium (0) (150 mg) were heated to reflux and reacted for 6 hours in a mixture of 2 M sodium carbonate aqueous solution (10 ml), toluene (10 ml) and ethanol (10 ml). After cooling to room temperature, water was added and extraction was performed with ethyl acetate. The ethyl acetate layer was washed with saturated saline and dried over magnesium sulfate, and the solvent was distilled off. The residue was purified by silica gel chromatography (200 g, hexane:ethyl acetate=4:1) to obtain 880 mg of 4-(6-cyano-2-naphthyloxy)-3-(2-formylphenyl)nitrobenzene.

후처리

  1. temperaturewere heated
  2. temperatureto reflux
  3. extractionextraction
  4. washThe ethyl acetate layer was washed with saturated saline
  5. dry with materialdried over magnesium sulfate
  6. distillationthe solvent was distilled off
  7. customThe residue was purified by silica gel chromatography (200 g, hexane:ethyl acetate=4:1)

출처 및 근거

ORD 기록
ord-00b3f9566f0247e989e5a7f00222f09f
출처 데이터셋
uspto-grants-2005_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06916837B2

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