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

HRID 1482026노트

반응식

HRID 1482026 반응식
[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]

참가 물질

6

반응물 4

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

생성물 1

HCID 1409612-Bromo-4,5-dimethylphenol수율 100.2%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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).

후처리

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

출처 및 근거

ORD 기록
ord-d588833ae2e440f2b31daa8307482aa8
출처 데이터셋
uspto-grants-2016_08
특허 번호
US09409922B2

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