Methanol → 2-((4-Bromobenzyl)amino)ethanol

HRID 1792417

反応式

HRID 1792417 の反応式
CN(CCO)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.CO.[Br:14]Br.C([N:18]([CH2:21]C)CC)C.[C:23]([O:26]CC)(=O)[CH3:24]>C(Cl)Cl.[Cl-].C([N+](CC)(CC)CC)C>[Br:14][C:3]1[CH:4]=[CH:5][C:6]([CH2:21][NH:18][CH2:24][CH2:23][OH:26])=[CH:7][CH:8]=1

参加物

8

反応物 5

HCID 887MethanolHCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 24408Bromine2 回HCID 623402-(N-Methylanilino)ethanol

生成物 1

HCID 4079852-((4-Bromobenzyl)amino)ethanol収率 75%

試薬・触媒・溶媒 2

HCID 5946Tetraethylammonium Chloride触媒HCID 6344Dichloromethane溶媒2 回

実験手順

To a solution of 2-(N-methylanilino)ethanol (0.76 g, 5 mmol) in methylene chloride (5 mL) were added tetraethylammonium chloride (83.0 mg, 0.5 mmol) and 0.1 mL of methanol. While stirring, a solution of bromine (0.8 g, 5 mmol) in methylene chloride (5 mL) was added slowly in a period of 5 minutes. When the color of the bromine persisted, triethylamine (0.75 mL) was added dropwise. The reaction mixture was diluted by ethyl acetate, washed with saturated sodium bicarbonate and brine, dried, and concentrated under reduced pressure to give 1.31 g of crude product which contained some 2,6-dibromo derivative. Flash chromatography of the crude mixture (35% ethyl acetate/hexane) gave 0.87 g (75%) of the desired product.

後処理

  1. washwashed with saturated sodium bicarbonate and brine
  2. customdried
  3. concentrationconcentrated under reduced pressure
  4. customto give 1.31 g of crude product which

出典と根拠

ORDレコード
ord-b331bea50b8341399b359a762691f74c
出典データセット
uspto-grants-2006_07
特許番号
US07074819B2

関連ノート

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