Phosphorus tribromide → 2-Bromo-5-(2-bromoethyl)pyridine

HRID 1400904ノート

反応式

HRID 1400904 の反応式
[Br:1][C:2]1[N:7]=[CH:6][C:5]([CH2:8][CH2:9]O)=[CH:4][CH:3]=1.P(Br)(Br)[Br:12]>C(Cl)Cl>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][CH2:9][Br:12])=[CH:6][N:7]=1

参加物

4

反応物 2

HCID 24614Phosphorus tribromideHCID 224732202-(6-Bromopyridin-3-yl)ethanol

生成物 1

HCID 584744292-Bromo-5-(2-bromoethyl)pyridine収率 87.8%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

Alcohol 289 (1.75 g, 8.66 mmol) was treated with phosphorous tribromide (5.0 mL, 53 mmol) and the mixture was heated for 5 min, until the solid had melted and re-solidified. The mixture was cooled, treated with ice and partitioned between saturated aqueous sodium bicarbonate and dichloromethane. The organic phase was collected, washed with saturated aqueous sodium bicarbonate and brine, dried (anhydrous MgSO4), filtered and concentrated. Silica gel chromatography of the residue (eluent DCM) provided title compound 290 (2.0 g, 7.6 mmol, 87% yield) as a colorless solid. MS (M+H): 266.0

後処理

  1. temperaturethe mixture was heated for 5 min, until the solid
  2. temperatureThe mixture was cooled
  3. additiontreated with ice
  4. custompartitioned between saturated aqueous sodium bicarbonate and dichloromethane
  5. customThe organic phase was collected
  6. washwashed with saturated aqueous sodium bicarbonate and brine
  7. dry with materialdried (anhydrous MgSO4)
  8. filtrationfiltered
  9. concentrationconcentrated

出典と根拠

ORDレコード
ord-13241e01ffea42919998fe0650decba0
出典データセット
uspto-grants-2014_12
特許番号
US08906852B2

反応ノート

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