Ethanolamine → 2-[(4-Bromo-3-methylphenyl)amino]ethan-1-ol

HRID 1754916노트

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HRID 1754916 반응식
[Br:1][C:2]1[CH:7]=[CH:6][C:5](I)=[CH:4][C:3]=1[CH3:9].[NH2:10][CH2:11][CH2:12][OH:13].N1CCC[C@H]1C(O)=O.C([O-])([O-])=O.[K+].[K+]>CS(C)=O.CCOC(C)=O.[Cu]I>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:10][CH2:11][CH2:12][OH:13])=[CH:4][C:3]=1[CH3:9]

참가 물질

8

반응물 4

HCID 700EthanolamineHCID 11430Potassium CarbonateHCID 145742L-ProlineHCID 27355742-Bromo-5-iodotoluene

생성물 1

HCID 285749422-[(4-Bromo-3-methylphenyl)amino]ethan-1-ol수율 81%

시약·촉매·용매 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 679Dimethyl Sulfoxide용매HCID 8857Ethyl Acetate용매

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온도
60 °C

실험 절차

A mixture of 2-bromo-5-iodotoluene (1.60 g, 5.40 mmol), 2-aminoethanol (0.49 mL, 8.14 mmol), CuI (53.3 mg, 0.28 mmol), L-proline (63.4 mg, 0.55 mmol) and K2CO3 (1.49 g, 10.8 mmol) in DMSO (3.24 mL) was stirred at 60° C. for 12 hours. The reaction mixture was cooled and then diluted with AcOEt, and the organic layer was sequentially washed with H2O and saturated brine. The organic layer was dried over Na2SO4 and then concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (hexane/AcOEt=1/1) to give 2-(4-bromo-3-methyl-phenylamino)-ethanol as a brown solid (1.00 g, 81%).

후처리

  1. temperatureThe reaction mixture was cooled
  2. washthe organic layer was sequentially washed with H2O and saturated brine
  3. dry with materialThe organic layer was dried over Na2SO4
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting residue was purified by silica gel column chromatography (hexane/AcOEt=1/1)

출처 및 근거

ORD 기록
ord-13de300069af41e199aa40862afcac30
출처 데이터셋
uspto-grants-2015_10
특허 번호
US09169254B2

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