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

HRID 1059509노트

반응식

HRID 1059509 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 1140Toluene용매

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온도
80 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-f65688546dc34d13b3d4134782b45fcc
출처 데이터셋
uspto-grants-2003_02
특허 번호
US06521605B1

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