Sulfuric Acid → 1-Bromo-4-(2-nitroprop-1-en-1-yl)benzene

HRID 1059509ノート

反応式

HRID 1059509 の反応式
[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=O)=[CH:4][CH:3]=1.[N+:10]([CH2:13][CH3:14])([O-:12])=[O:11].C([O-])(=O)C.[NH4+].S(=O)(=O)(O)O>C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[C:13]([N+:10]([O-:12])=[O:11])[CH3:14])=[CH:4][CH:3]=1

参加物

6

反応物 4

HCID 1118Sulfuric AcidHCID 6587NitroethaneHCID 707414-BromobenzaldehydeHCID 517165Ammonium Acetate

生成物 1

HCID 534140351-Bromo-4-(2-nitroprop-1-en-1-yl)benzene収率 47.7%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

反応条件

温度
80 °C

実験手順

A solution of 30.0 g (162 mmol) of 4-bromobenzaldehyde, 116 mL (1.6 mole) of nitroethane, and 37.5 g (486 mmol) of ammonium acetate in 200 mL of toluene was heated under a Dean and Stark trap for 18 hours. The mixture was then cooled to 80° C., 1 mL of concentrated sulfuric acid was added, and the mixture was stirred at 80° C. for 2 hours. The mixture was then cooled to ambient temperature and washed with 200 mL of brine. The organic layer was separated and the aqueous layer was extracted three times with 60 mL of diethyl ether. The combined organics were dried (MgSO4), filtered and concentrated in vacuo. The residue was recrystallized from methanol to afford 18.7 g (47%) of the title compound.

後処理

  1. temperatureThe mixture was then cooled to ambient temperature
  2. washwashed with 200 mL of brine
  3. customThe organic layer was separated
  4. extractionthe aqueous layer was extracted three times with 60 mL of diethyl ether
  5. dry with materialThe combined organics were dried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue was recrystallized from methanol

出典と根拠

ORDレコード
ord-f65688546dc34d13b3d4134782b45fcc
出典データセット
uspto-grants-2003_02
特許番号
US06521605B1

反応ノート

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