2-Bromo-4-methylphenol → 2-Bromo-4-methyl-6-nitrophenol

HRID 384323

반응식

HRID 384323 반응식
[N+:1]([O-:4])([O-])=[O:2].[Na+].[Br:6][C:7]1[CH:12]=[C:11]([CH3:13])[CH:10]=[CH:9][C:8]=1[OH:14]>S(=O)(=O)(O)O.O>[Br:6][C:7]1[CH:12]=[C:11]([CH3:13])[CH:10]=[C:9]([N+:1]([O-:4])=[O:2])[C:8]=1[OH:14]

참가 물질

5

반응물 2

HCID 231092-Bromo-4-methylphenolHCID 24268Sodium Nitrate

생성물 1

HCID 299182-Bromo-4-methyl-6-nitrophenol수율 29,045.199%

시약·촉매·용매 2

HCID 962Water용매HCID 1118Sulfuric Acid용매

실험 절차

Sodium nitrate (28 g, 0.33 mmol) was dissolved in the solvent mixture of 70 mL of concentrated sulfuric acid and 210 mL of water at −5° C., followed by slowly dropwise addition of 2-bromo-4-methyl-phenol 11a (30.8 g, 0.165 mol). The reaction mixture was reacted for 2 hours upon cooling by an ice-water bath. The mixture was warmed up to room temperature and reacted for another 1 hour. The reaction was monitored by TLC until the disappearance of the starting materials. The mixture was extracted with 200 mL of ethyl acetate. The combined organic extracts were washed with water (100 mL×5), dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by silica gel column chromatography to obtain the title compound 2-bromo-4-methyl-6-nitro-phenol 11b (22.24 g, yield 58.1%) as a yellow solid.

후처리

  1. customThe reaction mixture was reacted for 2 hours
  2. temperatureupon cooling by an ice-water bath
  3. customreacted for another 1 hour
  4. extractionThe mixture was extracted with 200 mL of ethyl acetate
  5. washThe combined organic extracts were washed with water (100 mL×5)
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was purified by silica gel column chromatography

출처 및 근거

ORD 기록
ord-ae8cdedc8c054f82beef374db0c36f0c
출처 데이터셋
uspto-grants-2013_02
특허 번호
US08367710B2

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