Methyl iodide → Methyl 5-bromo-2-methoxy-3-methylbenzoate

HRID 1771693

반응식

HRID 1771693 반응식
[Br:1][C:2]1[CH:3]=[C:4](C)[C:5](O)=[C:6]([CH:10]=1)[C:7](O)=O.[C:13]([O-:16])([O-])=[O:14].[K+].[K+].[CH3:19]I.[C:21]([O-:24])([O-])=O.[Cs+].[Cs+]>CC(C)=O.CN(C=O)C.O>[Br:1][C:2]1[CH:10]=[C:6]([CH3:7])[C:5]([O:24][CH3:21])=[C:4]([CH:3]=1)[C:13]([O:16][CH3:19])=[O:14]

참가 물질

8

반응물 4

HCID 6328Methyl iodide2회HCID 10796Cesium carbonateHCID 11430Potassium CarbonateHCID 27643455-Bromo-2-hydroxy-3-methylbenzoic acid

생성물 1

HCID 2764346Methyl 5-bromo-2-methoxy-3-methylbenzoate수율 77.8%

시약·촉매·용매 3

HCID 180Acetone용매HCID 962Water용매2회HCID 6228Dimethylformamide용매

반응 조건

온도
58 °C

실험 절차

To a solution of 5-bromo-2-hydroxy-3-methyl-benzoic acid (3 g, 12.9 mmol, 1.0 eq) and K2CO3 (5.38 g, 38.9 mmol, 3.0 eq) in acetone (15 mL) was added MeI (5.53 g, 38.9 mmol, 3.0 eq). The mixture was stirred at 58° C. overnight. TLC indicated that the reaction was not completed. Water was added and the aqueous layer extracted with EtOAc. The organic extract was washed with water and brine, dried (Na2SO4) filtered and evaporated in vacuo. The crude solid obtained was dissolved in DMF (20 mL) and Cs2CO3 (6 g, 18.4 mmol, 1.4 eq) added. To the mixture was added MeI (2 mL, 38.95 mmol, 3 eq). The mixture was stirred for 1 h at room temperature, water was added and the aqueous layer was extracted with EtOAc. The combined organic extracts were washed with water and brine, dried (Na2SO4), filtered and evaporated in vacuo to give the title compound as a white solid (2.6 g, 77%).

후처리

  1. extractionthe aqueous layer extracted with EtOAc
  2. extractionThe organic extract
  3. washwas washed with water and brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. customevaporated in vacuo
  7. customThe crude solid obtained
  8. stirringThe mixture was stirred for 1 h at room temperature
  9. extractionthe aqueous layer was extracted with EtOAc
  10. washThe combined organic extracts were washed with water and brine
  11. dry with materialdried (Na2SO4)
  12. filtrationfiltered
  13. customevaporated in vacuo

출처 및 근거

ORD 기록
ord-a137cbb6b8e94faca9e92d005cb5808b
출처 데이터셋
uspto-grants-2016_02
특허 번호
US09249085B2

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