Sulfuric Acid → Methyl 3-bromo-5-nitrobenzoate

HRID 1071959

반응식

HRID 1071959 반응식
[N+:1]([C:4]1[CH:5]=[C:6]([CH:11]=[CH:12][CH:13]=1)[C:7]([O:9][CH3:10])=[O:8])([O-:3])=[O:2].S(=O)(=O)(O)O.[Br:19]Br>S(=O)(=O)(O)O.S([O-])([O-])(=O)=O.[Ag+2].CO>[Br:19][C:12]1[CH:11]=[C:6]([CH:5]=[C:4]([N+:1]([O-:3])=[O:2])[CH:13]=1)[C:7]([O:9][CH3:10])=[O:8]

참가 물질

7

반응물 3

HCID 1118Sulfuric AcidHCID 24408BromineHCID 69260Methyl 3-nitrobenzoate

생성물 1

HCID 239341Methyl 3-bromo-5-nitrobenzoate수율 72%

시약·촉매·용매 3

HCID 1118Sulfuric Acid촉매HCID 178418844HCID 178418844, 화합물촉매HCID 887Methanol용매

반응 조건

온도
90 °C

실험 절차

A mixture of methyl 3-nitrobenzoate (122 g, 674 mmol), silver sulphate (100 g, 320.7 mmol) and concentrated sulfuric acid (750 mL) was stirred mechanically and heated at 90° C. To this mixture was added bromine (37 mL), dropwise, over 2 h. The reaction was stirred another hour, cooled and filtered. The filtrate was mixed with 2 L water and 1 Kg crushed ice. The solid was filtered and dried to afford a mixture of the desired methyl ester and free acid hydrolysis product. The mixture was taken up into methanol (1 L), treated with 10 drops concentrated sulfuric acid and refluxed for 12 h. The reaction mixture was allowed to cool and the crystals that were deposited were collected and dried in a desiccator to afford 126 g (72% yield) of methyl 3-bromo-5-nitrobenzoate (EX-119A): 1H NMR (300 MHz, CDCl3) δ 8.65 (s, 1 H), 8.44 (s, 1 H), 8.37 (s, 1 H), 3.94 (s, 3H).

후처리

  1. stirringThe reaction was stirred another hour
  2. temperaturecooled
  3. filtrationfiltered
  4. additionThe filtrate was mixed with 2 L water and 1 Kg
  5. customcrushed ice
  6. filtrationThe solid was filtered
  7. customdried
  8. customto afford
  9. temperaturerefluxed for 12 h
  10. temperatureto cool
  11. customthe crystals that were deposited were collected
  12. customdried in a desiccator

출처 및 근거

ORD 기록
ord-aad666afc1da407fb87b99859c5f9a8a
출처 데이터셋
uspto-grants-2005_06
특허 번호
US06908919B2

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