Benzyl Bromide → Dibenzyl-(4-iodo-2,5-dimethylphenyl)amine

HRID 1055324노트

반응식

HRID 1055324 반응식
[CH3:1][C:2]1[CH:8]=[C:7]([I:9])[C:6]([CH3:10])=[CH:5][C:3]=1[NH2:4].[CH2:11](Br)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C(=O)([O-])[O-].[K+].[K+]>CCO>[CH2:11]([N:4]([CH2:1][C:2]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:3]=1)[C:3]1[CH:5]=[C:6]([CH3:10])[C:7]([I:9])=[CH:8][C:2]=1[CH3:1])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

참가 물질

5

반응물 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 4770984(4-Iodo-2,5-Dimethylphenyl)Amine

생성물 1

HCID 57461072Dibenzyl-(4-iodo-2,5-dimethylphenyl)amine수율 167.7%

시약·촉매·용매 1

HCID 702Ethanol용매

반응 조건

온도
50 °C

실험 절차

A mixture of 2,5-dimethyl-4-iodoaniline (6.44 g, 26.1 mmol), benzyl bromide (11.50 g, 67.24 mmol) and potassium carbonate (8.20 g, 59.3 mmol) in EtOH (100 mL) was stirred at 50° C. for 12 h. The reaction mixture was then concentrated under reduced pressure. The residue (a purple solid) was mixed with DCM and this mixture was filtered using vacuum. The filtrate was purified by silica gel flash chromatography (0-5% MeOH in DCM) to give the title compound (9.35 g, 83% yield) as an oil.

후처리

  1. concentrationThe reaction mixture was then concentrated under reduced pressure
  2. additionThe residue (a purple solid) was mixed with DCM
  3. filtrationthis mixture was filtered
  4. customThe filtrate was purified by silica gel flash chromatography (0-5% MeOH in DCM)

출처 및 근거

ORD 기록
ord-7ef8022c61c04f06b78996a02314811d
출처 데이터셋
uspto-grants-2016_07
특허 번호
US09394275B2

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