Dimethylformamide → 3-Cyano-4-(trifluoromethoxy)benzaldehyde

HRID 2269250노트

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HRID 2269250 반응식
I[C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[O:10][C:11]([F:14])([F:13])[F:12])[CH:5]=[O:6].[CH3:15][N:16](C=O)C>C1(C)C=CC=CC=1.[C-]#N.[Zn+2].[C-]#N.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>[C:15]([C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[O:10][C:11]([F:14])([F:13])[F:12])[CH:5]=[O:6])#[N:16]

참가 물질

6

반응물 2

HCID 6228DimethylformamideHCID 183336193-Iodo-4-(trifluoromethoxy)benzaldehyde

생성물 1

HCID 186776033-Cyano-4-(trifluoromethoxy)benzaldehyde

시약·촉매·용매 3

HCID 11186Zinc cyanide (Zn(CN)2)촉매HCID 178418397HCID 178418397, 화합물촉매HCID 1140Toluene용매

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온도
100 °C

실험 절차

To a stirred suspension of Compound 19 (6.85 g, 21.7 mmol) and zinc cyanide (4.07 g, 34.7 mmol) in dry DMF (35 ml) was added tetrakis(triphenylphosphine)palladium(0) (3.00 g, 2.60 mmol) portionwise at room temperature. The reaction mixture was heated at 100° C. for 9 h. The reaction mixture was diluted with toluene (100 ml)-2M NH3 aq. (100 ml). The organic layer was separated. The aqueous layer was diluted with toluene (100 ml), filtered through a pad of celite and the filter cake was washed with toluene. The organic layer was separated and the aqueous layer was extracted with toluene. The combined solution was washed with 2M NH3 aq. (50 ml) and brine, dried (MgSO4), and concentrated in vacuo to give crude product as a dark tan oil.

후처리

  1. customThe organic layer was separated
  2. additionThe aqueous layer was diluted with toluene (100 ml)
  3. filtrationfiltered through a pad of celite
  4. washthe filter cake was washed with toluene
  5. customThe organic layer was separated
  6. extractionthe aqueous layer was extracted with toluene
  7. washThe combined solution was washed with 2M NH3 aq. (50 ml) and brine
  8. dry with materialdried (MgSO4)
  9. concentrationconcentrated in vacuo
  10. customto give crude product as a dark tan oil

출처 및 근거

ORD 기록
ord-88542c3d4a20409d8e1c9aed903c1f7c
출처 데이터셋
uspto-grants-2001_12
특허 번호
US06329396B1

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