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

HRID 1792417

반응식

HRID 1792417 반응식
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

참가 물질

8

반응물 5

HCID 887MethanolHCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 24408Bromine2회HCID 623402-(N-Methylanilino)ethanol

생성물 1

HCID 4079852-((4-Bromobenzyl)amino)ethanol수율 75%

시약·촉매·용매 2

HCID 5946Tetraethylammonium Chloride촉매HCID 6344Dichloromethane용매2회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-b331bea50b8341399b359a762691f74c
출처 데이터셋
uspto-grants-2006_07
특허 번호
US07074819B2

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