Toluene → 2-(Bromomethyl)-5-nitrothiophene

HRID 861881ノート

反応式

HRID 861881 の反応式
P(Br)(Br)[Br:2].O[CH2:6][C:7]1[S:8][C:9]([N+:12]([O-:14])=[O:13])=[CH:10][CH:11]=1.C1(C)C=CC=CC=1>O>[Br:2][CH2:6][C:7]1[S:8][C:9]([N+:12]([O-:14])=[O:13])=[CH:10][CH:11]=1

参加物

5

反応物 3

HCID 1140TolueneHCID 24614Phosphorus tribromideHCID 332588(5-nitrothiophen-2-yl)methanol

生成物 1

HCID 536851562-(Bromomethyl)-5-nitrothiophene収率 261.6%

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
70 °C

実験手順

Phosphorus tribromide (PBr3) (10.45 g) was added dropwise to a mixture of 2-hydroxymethyl-5-nitrothiophene (17.7 g) and toluene (150 ml) and this mixture was stirred at 70° C. for 1.5 hours. The reaction mixture was poured into water and extracted with ether. The ether layer was washed with water and dried (MgSO4), after which the solvent was evaporated off. The residual oil was subjected to solica gel column chromatography and eluted with chloroform to yield 2-bromomethyl-5-nitrothiophene (22.43 g, 92%) as an oil.

後処理

  1. extractionextracted with ether
  2. washThe ether layer was washed with water
  3. dry with materialdried (MgSO4)
  4. customafter which the solvent was evaporated off
  5. washeluted with chloroform

出典と根拠

ORDレコード
ord-98cdb1d533454e5390c0078761500449
出典データセット
uspto-grants-1998_02
特許番号
US05716944

反応ノート

読み込み中…