Hydrochloric Acid → 5-Methoxy-2-nitro-4-(trifluoromethyl)benzene acetonitrile

HRID 427727

反応式

HRID 427727 の反応式
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N+:9]([O-:11])=[O:10])=[CH:5][C:4]=1[C:12]([F:15])([F:14])[F:13].Cl[CH:17](OC1C=CC=CC=1)[C:18]#[N:19].CC([O-])(C)C.[K+].Cl>CN(C=O)C>[CH3:1][O:2][C:3]1[C:4]([C:12]([F:13])([F:14])[F:15])=[CH:5][C:6]([N+:9]([O-:11])=[O:10])=[C:7]([CH2:17][C:18]#[N:19])[CH:8]=1

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 695624-Nitro-2-(trifluoromethyl)anisoleHCID 23665647Potassium tert-butoxideHCID 53400486Chlorophenoxyacetonitrile

生成物 1

HCID 107777195-Methoxy-2-nitro-4-(trifluoromethyl)benzene acetonitrile収率 78%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒2 回

反応条件

温度
-10 °C

実験手順

A mixture of 1-Methoxy4-nitro-2-trifluoromethylbenzene (93 g, 0.421 mol) and 4 chlorophenoxyacetonitrile (77.55 g, 0.463 mol) in dry DMF (500 ml) was added dropwise over 0.75 h to a stirred solution of KOtBu (103.85 g, 0.927 mol) in dry DMF (400 ml) at −10° C. After complete addition the resulting purple solution was maintained at −10° C. for 1 h then poured into a mixture of ice/water (1.5 l) and 5 M aqueous HCl (1.5 l). The resulting mixture was extracted with dichloromethane (3×1 l). The combined extracts were washed with water (3 l), dried (Na2SO4) and evaporated under reduced pressure. The residue was chromatographed on silica using 10-40% ethyl acetate/petroleum ether as eluant to give the crude product which was recrystallised from ethyl acetate/petroleum ether to afford the title compound (85.13 g, 78%) as a white solid. Mp 103-104° C.

後処理

  1. additionAfter complete addition the resulting purple solution
  2. extractionThe resulting mixture was extracted with dichloromethane (3×1 l)
  3. washThe combined extracts were washed with water (3 l)
  4. dry with materialdried (Na2SO4)
  5. customevaporated under reduced pressure
  6. customThe residue was chromatographed on silica using 10-40% ethyl acetate/petroleum ether as eluant
  7. customto give the crude product which
  8. customwas recrystallised from ethyl acetate/petroleum ether

出典と根拠

ORDレコード
ord-600541f8065d45c5ac36de639037f837
出典データセット
uspto-grants-2001_11
特許番号
US06313145B1

関連ノート

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