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

HRID 2269250ノート

反応式

HRID 2269250 の反応式
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]

参加物

6

反応物 2

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

生成物 1

HCID 186776033-Cyano-4-(trifluoromethoxy)benzaldehyde

試薬・触媒・溶媒 3

HCID 11186Zinc cyanide (Zn(CN)2)触媒HCID 178418397HCID 178418397、化合物触媒HCID 1140Toluene溶媒

反応条件

温度
100 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-88542c3d4a20409d8e1c9aed903c1f7c
出典データセット
uspto-grants-2001_12
特許番号
US06329396B1

反応ノート

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