Dimethylformamide → 6-Bromo-2,3-dimethoxybenzaldehyde

HRID 2290916노트

반응식

HRID 2290916 반응식
[Br:1][C:2]1[C:7]([CH:8]=[O:9])=[C:6]([OH:10])[C:5]([O:11][CH3:12])=[CH:4][CH:3]=1.[C:13]([O-])([O-])=O.[K+].[K+].CN(C=O)C.COS(OC)(=O)=O>O>[Br:1][C:2]1[C:7]([CH:8]=[O:9])=[C:6]([O:10][CH3:13])[C:5]([O:11][CH3:12])=[CH:4][CH:3]=1

참가 물질

6

반응물 4

HCID 6228DimethylformamideHCID 6497Dimethyl SulfateHCID 11430Potassium CarbonateHCID 2622376-Bromo-2-hydroxy-3-methoxybenzaldehyde

생성물 1

HCID 46719526-Bromo-2,3-dimethoxybenzaldehyde

시약·촉매·용매 1

HCID 962Water용매

실험 절차

A mixture of 6-bromo-2-hydroxy-3-methoxybenzaldehyde (66.8 g, 0.29 mole), K2CO3 (powdered, 79 g, 0.57 mole), and dry DMF (250 mL) was stirred under N2 at 110° as dimethylsulfate (33.5 mL, 0.35 mole) was added dropwise. The reaction mixture was stirred at 135° for 5 hours, was cooled to room temperature, and water was added. The aqueous mixture was extracted with CH2Cl2. The combined extracts were washed with water, saturated aqueous NaCl, dried (MgSO4), filtered, and evaporated to yield ca 80 g. tan solid. The crude product was recrystallized from 2-propanol to obtain 55.2 g cream colored solid, (77%); mp 92°-3°.

후처리

  1. additionwas added dropwise
  2. extractionThe aqueous mixture was extracted with CH2Cl2
  3. washThe combined extracts were washed with water, saturated aqueous NaCl
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customevaporated
  7. customto yield ca 80 g
  8. customThe crude product was recrystallized from 2-propanol
  9. customto obtain 55.2 g cream colored solid, (77%)

출처 및 근거

ORD 기록
ord-e49f7c7ef24842b6a6a85a1fdd0dbdd9
출처 데이터셋
uspto-grants-1986_10
특허 번호
US04618683

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