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

HRID 384323

反応式

HRID 384323 の反応式
[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]

参加物

5

反応物 2

HCID 231092-Bromo-4-methylphenolHCID 24268Sodium Nitrate

生成物 1

HCID 299182-Bromo-4-methyl-6-nitrophenol収率 29,045.199%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 1118Sulfuric Acid溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-ae8cdedc8c054f82beef374db0c36f0c
出典データセット
uspto-grants-2013_02
特許番号
US08367710B2

関連ノート

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