3,4-Dimethylphenol → 2-Bromo-4,5-dimethylphenol

HRID 1482026ノート

反応式

HRID 1482026 の反応式
[CH3:1][C:2]1[CH:3]=[C:4]([OH:9])[CH:5]=[CH:6][C:7]=1[CH3:8].CC(O)C.C(=O)=O.[Br:17]Br.[O-]S([O-])=O.[Na+].[Na+]>C(Cl)Cl>[Br:17][C:5]1[CH:6]=[C:7]([CH3:8])[C:2]([CH3:1])=[CH:3][C:4]=1[OH:9]

参加物

6

反応物 4

HCID 72493,4-DimethylphenolHCID 24408BromineHCID 24437Sodium SulfiteHCID 86586944Isopropanol carbon dioxide

生成物 1

HCID 1409612-Bromo-4,5-dimethylphenol収率 100.2%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a solution of 3,4-dimethylphenol (2.48 g, 20.3 mmol, 1 equiv) in DCM (200 mL) at −78° C. (IPA/dry ice) was added dropwise bromine (1.05 mL, 20.3 mmol, 1 equiv). After 1 h, 1 N Na2SO3 was added and the cold bath was removed. After warming to ambient temperature, the DCM layer was separated, dried (Na2SO4), and concentrated in vacuo to provide the product (4.09 g, 100%) as a yellow solid. Regioselectivity>10:1, use as is. 1H NMR (400 MHz, CDCl3) δ 7.21 (s, 1H), 6.83 (s, 1H), 5.26 (s, 1H), 2.20 (s, 3H), 2.18 (s, 3H).

後処理

  1. customthe cold bath was removed
  2. customthe DCM layer was separated
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-d588833ae2e440f2b31daa8307482aa8
出典データセット
uspto-grants-2016_08
特許番号
US09409922B2

反応ノート

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