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

HRID 221922

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HRID 221922 반응식
[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]

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 962Water용매

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온도
150 °C

실험 절차

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%).

후처리

  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))

출처 및 근거

ORD 기록
ord-1c17dcd5465d4098b149d97cecfc02db
출처 데이터셋
uspto-grants-2012_06
특허 번호
US08207134B2

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