Nitric Acid → 1-Bromo-4-fluoro-2-methyl-5-nitrobenzene

HRID 522705

반응식

HRID 522705 반응식
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[CH3:9].[N+:10]([O-])([OH:12])=[O:11]>S(=O)(=O)(O)O>[Br:1][C:2]1[CH:7]=[C:6]([N+:10]([O-:12])=[O:11])[C:5]([F:8])=[CH:4][C:3]=1[CH3:9]

참가 물질

4

반응물 2

HCID 944Nitric AcidHCID 967432-Bromo-5-fluorotoluene

생성물 1

HCID 100369831-Bromo-4-fluoro-2-methyl-5-nitrobenzene수율 104.8%

시약·촉매·용매 1

HCID 1118Sulfuric Acid용매

실험 절차

Combine 1-bromo-4-fluoro-2-methylbenzene (30.0 g, 159 mmol) in concentrated sulfuric acid (100 mL), cool to about −5° C., and treat dropwise with nitric acid (11.00 mL, 174 mmol) over 20 minutes. Allow reaction mixture to warm to RT and stir for 30 min. Pour onto crushed ice with stirring and partition with tert-butyl methyl ether (MTBE) (200 mL). Separate the aqueous layer and extract with MTBE (2×50 mL). Combine organic layers, dry and concentrate under reduced pressure to provide 1-bromo-4-fluoro-2-methyl-5-nitrobenzene as an orange-colored viscous oil (39.0 g).

후처리

  1. customAllow reaction mixture
  2. additionPour
  3. customonto crushed ice
  4. stirringwith stirring
  5. custompartition with tert-butyl methyl ether (MTBE) (200 mL)
  6. customSeparate the aqueous layer
  7. extractionextract with MTBE (2×50 mL)
  8. customCombine organic layers, dry
  9. concentrationconcentrate under reduced pressure

출처 및 근거

ORD 기록
ord-10aeb7632329498392241d80648555f9
출처 데이터셋
uspto-grants-2016_05
특허 번호
US09334267B2

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