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

HRID 1754916ノート

反応式

HRID 1754916 の反応式
[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]

参加物

8

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 679Dimethyl Sulfoxide溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
60 °C

実験手順

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%).

後処理

  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)

出典と根拠

ORDレコード
ord-13de300069af41e199aa40862afcac30
出典データセット
uspto-grants-2015_10
特許番号
US09169254B2

反応ノート

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