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Sodium Carbonate → Benzyl 2-benzyloxy-5-cyanobenzoate

HRID 1639535
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인쇄 미리보기

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HRID 1639535 반응식
[CH2:1]([O:8][C:9]1[CH:24]=[CH:23][C:22](Br)=[CH:21][C:10]=1[C:11]([O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[Na+].[Na+].C[C:33]([N:35](C)C)=O>O.[C-]#N.[C-]#N.[C-]#N.[C-]#N.[C-]#N.[C-]#N.O.O.O.[K+].[K+].[K+].[K+].[Fe+2].C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH2:1]([O:8][C:9]1[CH:24]=[CH:23][C:22]([C:33]#[N:35])=[CH:21][C:10]=1[C:11]([O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 3

HCID 10340Sodium CarbonateHCID 31374DimethylacetamideHCID 17750009Benzyl 2-(benzyloxy)-5-bromobenzoate

생성물 1

HCID 18974028Benzyl 2-benzyloxy-5-cyanobenzoate수율 72%

시약·촉매·용매 3

HCID 161067Potassium ferrocyanide trihydrate촉매
HCID 167845
palladium(II) acetate
촉매
HCID 962Water용매

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온도
120 °C

실험 절차

A mixture of 695 mg (1.76 mmol) of benzyl 2-benzyloxy-5-bromobenzoate, 175 mg (0.41 mmol) of potassium hexacyanoferrate(II) trihydrate, 41 mg (0.8 mmol) of palladium(II) acetate, and 189 mg (1.75 mmol) of sodium carbonate in 3 mL of dimethylacetamide is heated at 120° C. for 24 hrs. The reaction mixture is diluted with water and extracted several times with ethyl acetate. Combined extracts are washed with brine and dried over Na2SO4. After solvent removal by rotoevaporation, the crude product is purified by preparative TLC to give 436 mg (1.27 mmol, 72% yield) of benzyl 2-benzyloxy-5-cyanobenzoate.

후처리

  1. extractionextracted several times with ethyl acetate
  2. washCombined extracts are washed with brine
  3. dry with materialdried over Na2SO4
  4. customAfter solvent removal by rotoevaporation
  5. customthe crude product is purified by preparative TLC

출처 및 근거

ORD 기록
ord-05281bd2597847fd9a7a65b38c57c19f
출처 데이터셋
uspto-grants-2012_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08110570B2

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