P-Nitrobenzotrifluoride → (2-Nitro-5-trifluoromethylphenyl) acetonitrile

HRID 427724

反応式

HRID 427724 の反応式
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]([F:13])([F:12])[F:11])=[CH:6][CH:5]=1)([O-:3])=[O:2].ClC1C=CC(O[CH2:20][C:21]#[N:22])=CC=1.CC(C)([O-])C.[K+]>CN(C=O)C>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([C:10]([F:11])([F:12])[F:13])=[CH:8][C:9]=1[CH2:20][C:21]#[N:22])([O-:3])=[O:2]

参加物

5

反応物 3

HCID 9821P-NitrobenzotrifluorideHCID 3064442-(4-Chlorophenoxy)acetonitrileHCID 23665647Potassium tert-butoxide

生成物 1

HCID 18357729(2-Nitro-5-trifluoromethylphenyl) acetonitrile収率 32%

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

4-Nitrobenzotrifluoride (5 g, 0.026 mole) and 4-chlorophenoxyacetonitrile (4.86 g, 0.029 mole) in dry DMF (50 ml) were added dropwise to a solution of potassium-t-butoxide (6.4 g, 0.057 mole) in dry DMF (30 ml) under argon at −10° C. over 1 hour. The mixture was stirred at −10° C. for a further 3 hours, after which it was poured into 5N HCl/ice water (1:1) (300 ml) and extracted into DCM (3×200 ml). The DCM extract was washed with 10% aqueous sodium hydroxide solution, 5N hydrochloric acid and brine, dried (Na2SO4) and evaporated in vacuo. The resulting oil was chromatographed on silica gel eluting with 20% ethyl acetate/60-80° petroleum ether to afford the title compound (1.9 g, 32%) as an orange oil.

後処理

  1. extractionextracted into DCM (3×200 ml)
  2. extractionThe DCM extract
  3. washwas washed with 10% aqueous sodium hydroxide solution, 5N hydrochloric acid and brine
  4. dry with materialdried (Na2SO4)
  5. customevaporated in vacuo
  6. customThe resulting oil was chromatographed on silica gel eluting with 20% ethyl acetate/60-80° petroleum ether

出典と根拠

ORDレコード
ord-a98ff63aac5841e685b15ecb2b8f6a7d
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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