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

HRID 1373692

反応式

HRID 1373692 の反応式
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]

参加物

6

反応物 4

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

生成物 1

HCID 120160382-Bromo-4-(bromomethyl)benzaldehyde収率 113.1%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

反応条件

温度
0 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-0bd9025d21bc48a48f6af550443f2cde
出典データセット
uspto-grants-2007_01
特許番号
US07163932B2

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