Water → 2-Amino-5-bromobenzenemethanol

HRID 44189

반응식

HRID 44189 반응식
[H-].[Al+3].[Li+].[H-].[H-].[H-].[NH2:7][C:8]1[CH:17]=[CH:16][C:15]([Br:18])=[CH:14][C:9]=1[C:10](OC)=[O:11].O.[OH-].[Na+]>C1COCC1>[NH2:7][C:8]1[CH:17]=[CH:16][C:15]([Br:18])=[CH:14][C:9]=1[CH2:10][OH:11]

참가 물질

6

반응물 4

HCID 962Water2회HCID 14798Sodium HydroxideHCID 736224Methyl 2-amino-5-bromobenzoateHCID 21226445Aluminium lithium hydride

생성물 1

HCID 110308742-Amino-5-bromobenzenemethanol수율 59.8%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

To a suspension of lithium aluminium hydride (0.33 g, 8.7 mmol) in THF (10 ml) was added a solution of methyl 2-amino-5-bromobenzoate (2.0 g, 8.7 mmol) in 20 ml THF at 0° C. under nitrogen. Then stirring was continued for 2 h. 0.64 ml water, 2 M solution of sodium hydroxide (0.64 ml) and again 1.28 ml water were added before the resulting mixture was filtered through celite. Evaporation of the solvent and purification of the crude product by flash chromatography on silica gel (dichloromethane/ethyl acetate, 2/1) yielded (2-amino-5-bromophenyl)methanol (1.0 g, 5.2 mmol, 59%) as off-white solid.

후처리

  1. filtrationwas filtered through celite
  2. customEvaporation of the solvent and purification of the crude product by flash chromatography on silica gel (dichloromethane/ethyl acetate, 2/1)

출처 및 근거

ORD 기록
ord-eac0c260257f408f86bcc379c762a4e5
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08541404B2

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