Hydrochloric Acid → (5-Methoxy-2-nitrophenyl)acetonitrile

HRID 469287

反応式

HRID 469287 の反応式
CC(C)([O-])C.[K+].[N+:7]([C:10]1[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][CH:11]=1)([O-:9])=[O:8].ClC1C=CC(O[CH2:24][C:25]#[N:26])=CC=1.Cl>CN(C=O)C>[CH3:17][O:16][C:13]1[CH:14]=[CH:15][C:10]([N+:7]([O-:9])=[O:8])=[C:11]([CH2:24][C:25]#[N:26])[CH:12]=1

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 74854-NitroanisoleHCID 3064442-(4-Chlorophenoxy)acetonitrileHCID 23665647Potassium tert-butoxide

生成物 1

HCID 10867168(5-Methoxy-2-nitrophenyl)acetonitrile収率 39.3%

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

24.0 g (214 mmol) potassium-tert-butoxide in 100 mL DMF were slowly added dropwise to a solution of 13.17 g (86.0 mmol) 4-nitroanisole and 18.0 g (107 mmol) 4-chlorophenoxyacetonitrile in 50 mL DMF. The reaction mixture was stirred for 30 min at −10° C. and then poured into 300 g of a 1:1 mixture of conc. HCl and ice. After extraction with EtOAc the organic phase was washed with water, dried and concentrated to dryness by rotary evaporation in vacuo with gentle heating. The residue was treated with a 1:1 mixture of PE/EtOAc and the product that crystallised out was suction filtered. After washing with a 1:1 mixture of PE/EtOAc the crystals were dried in the air. 6.5 g of the desired product was obtained.

後処理

  1. extractionAfter extraction with EtOAc the organic phase
  2. washwas washed with water
  3. customdried
  4. concentrationconcentrated to dryness by rotary evaporation in vacuo with gentle heating
  5. additionThe residue was treated with a 1:1 mixture of PE/EtOAc
  6. customthe product that crystallised out
  7. filtrationfiltered
  8. washAfter washing with a 1:1 mixture of PE/EtOAc the crystals
  9. customwere dried in the air

出典と根拠

ORDレコード
ord-a5d428de0d334c369a4650bf0acf66ea
出典データセット
uspto-grants-2014_01
特許番号
US08629137B2

関連ノート

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