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Toluene → 7-Bromo-2-tert-butyl-6-(3-hydroxyphenyl)-5-methyl-1,3-benzoxazole-4-carbonitrile

HRID 17279
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HRID 17279 반응식
C1(C)C=CC=CC=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1.[Br:20][C:21]1[C:26]([OH:27])=[C:25]([NH:28][C:29](=O)[C:30]([CH3:33])([CH3:32])[CH3:31])[C:24]([C:35]#[N:36])=[C:23]([CH3:37])[C:22]=1[C:38]1[CH:43]=[CH:42][CH:41]=[C:40]([OH:44])[CH:39]=1>O>[Br:20][C:21]1[C:22]([C:38]2[CH:43]=[CH:42][CH:41]=[C:40]([OH:44])[CH:39]=2)=[C:23]([CH3:37])[C:24]([C:35]#[N:36])=[C:25]2[C:26]=1[O:27][C:29]([C:30]([CH3:32])([CH3:31])[CH3:33])=[N:28]2
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5

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HCID 1140TolueneHCID 521998p-Toluenesulfonic acid monohydrateHCID 86630804N-(2-Bromo-5-cyano-3,3'-dihydroxy-6-methylbiphenyl-4-yl)-2,2-dimethylpropionamide

생성물 1

HCID 685850047-Bromo-2-tert-butyl-6-(3-hydroxyphenyl)-5-methyl-1,3-benzoxazole-4-carbonitrile수율 95%

시약·촉매·용매 1

HCID 962Water용매

실험 절차

Toluene (45 ml), p-toluenesulfonic acid monohydrate (21.0 mg, 111 μmol) were added to N-(2-bromo-5-cyano-3,3′-dihydroxy-6-methylbiphenyl-4-yl)-2,2-dimethylpropionamide (I-16) (446 mg, 1.11 mmol), followed by refluxing with a Dean-Stark condenser for 3 hours. After cooling, water (50 ml) was added to the reaction liquid, the product was extracted with ethyl acetate (50 ml×2). The organic layer was washed with saturated brine (50 ml), dried over anhydrous magnesium sulfate, concentrated under reduced pressure, the residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=3:1) to obtain the entitled compound (404 mg, 95%) as a colorless solid.

후처리

  1. temperatureby refluxing with a Dean-Stark condenser for 3 hours
  2. temperatureAfter cooling
  3. extractionthe product was extracted with ethyl acetate (50 ml×2)
  4. washThe organic layer was washed with saturated brine (50 ml)
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customthe residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=3:1)

출처 및 근거

ORD 기록
ord-0bbb1f0ef9f34865b1c08f15cf05cf63
출처 데이터셋
uspto-grants-2010_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07737166B2

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