Dimethylformamide → 2-Bromo-4-(bromomethyl)benzaldehyde

HRID 1373692

반응식

HRID 1373692 반응식
P(Br)(Br)([Br:3])=O.CN(C=O)C.[Br:11][C:12]1[CH:19]=[C:18]([CH2:20]O)[CH:17]=[CH:16][C:13]=1[CH:14]=[O:15].C([O-])(O)=O.[Na+]>C(Cl)Cl>[Br:11][C:12]1[CH:19]=[C:18]([CH2:20][Br:3])[CH:17]=[CH:16][C:13]=1[CH:14]=[O:15]

참가 물질

6

반응물 4

HCID 6228DimethylformamideHCID 24613Phosphorus oxybromideHCID 516892Sodium BicarbonateHCID 183743722-Bromo-4-(hydroxymethyl)benzaldehyde

생성물 1

HCID 120160382-Bromo-4-(bromomethyl)benzaldehyde수율 113.1%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

반응 조건

온도
0 °C

실험 절차

To a stirring cold (0° C.) solution of POBr3 (0.6 mol, 171 g) in CH2Cl2 (1.6 L) was added dropwise DMF (0.75 L) over a period of 1 h. A solution of 2-bromo-4-hydroxymethyl-benzaldehyde (0.49 mol, 107 g) in CH2Cl2 (0.75 L) was then added dropwise over a period of 0.5 h. The resulting mixture was stirred at 0° C. for another 0.5 h and was then transferred via a cannula to a cold (0° C.) stirring aqueous solution of NaHCO3 (3 L, 1M) while maintaining the temperature of the aqueous solution below 10° C. After the transfer was completed, the mixture was extracted with CH2Cl2 (2 L). The organic extract was separated and washed with H2O (3 L) and brine (3 L), dried with MgSO4 (anhyd.) and concentrated to give an oil . The residue was extracted with 10% EtOAc/hexane (2 L). The organic extract was washed with H2O (2×1 L), dried with MgSO4 (anhyd.) and concentrated to a solid which was swished with hexane to give 154 g (˜100%) of the title compound as a beige solid.

후처리

  1. customwas then transferred via a cannula to a cold (0° C.)
  2. temperaturewhile maintaining the temperature of the aqueous solution below 10° C
  3. extractionthe mixture was extracted with CH2Cl2 (2 L)
  4. extractionThe organic extract
  5. customwas separated
  6. washwashed with H2O (3 L) and brine (3 L)
  7. dry with materialdried with MgSO4 (anhyd.)
  8. concentrationconcentrated
  9. customto give an oil
  10. extractionThe residue was extracted with 10% EtOAc/hexane (2 L)
  11. extractionThe organic extract
  12. washwas washed with H2O (2×1 L)
  13. dry with materialdried with MgSO4 (anhyd.)
  14. concentrationconcentrated to a solid which

출처 및 근거

ORD 기록
ord-0bd9025d21bc48a48f6af550443f2cde
출처 데이터셋
uspto-grants-2007_01
특허 번호
US07163932B2

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