Ethanol → (3-Bromo-4-methylphenyl)-(2,2-diethoxyethyl)-amine

HRID 221922

反応式

HRID 221922 の反応式
[Br:1][C:2]1[CH:3]=[C:4]([NH2:9])[CH:5]=[CH:6][C:7]=1[CH3:8].[CH2:10]([O:12][CH:13]([O:16][CH2:17][CH3:18])[CH2:14]Br)[CH3:11].C(N(CC)CC)C.C(O)C>O>[Br:1][C:2]1[CH:3]=[C:4]([NH:9][CH2:14][CH:13]([O:16][CH2:17][CH3:18])[O:12][CH2:10][CH3:11])[CH:5]=[CH:6][C:7]=1[CH3:8]

参加物

6

反応物 4

HCID 702EthanolHCID 8471TriethylamineHCID 74852Ethane, 2-bromo-1,1-diethoxy-HCID 82187Benzenamine, 3-bromo-4-methyl-

生成物 1

HCID 59488813(3-Bromo-4-methylphenyl)-(2,2-diethoxyethyl)-amine収率 80.1%

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
150 °C

実験手順

Under a nitrogen stream, a mixture of 3-bromo-4-methyl-phenylamine (4.94 g, 26.55 mmol), bromoacetaldehyde diethyl acetal (6.80 g, 34.50 mmol), triethylamine (5.37 mL, 38.53 mmol) and ethanol (10.3 mL) was stirred for 2 hours at 150° C. using a microwave apparatus. The resultant solution was cooled to room temperature, and then water was added thereto. The resultant mixture was extracted with dichloromethane. The organic layer was dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The resulting residue was purified by silica gel flash column chromatography (developing solution=ethyl acetate:n-hexane (1:10)), to thereby obtain the titled compound (6.43 g, 80%).

後処理

  1. extractionThe resultant mixture was extracted with dichloromethane
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe resulting residue was purified by silica gel flash column chromatography (developing solution=ethyl acetate:n-hexane (1:10))

出典と根拠

ORDレコード
ord-1c17dcd5465d4098b149d97cecfc02db
出典データセット
uspto-grants-2012_06
特許番号
US08207134B2

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