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Potassium Carbonate → N-(4-chlorophenethyl)-4-(2-bromo-4-formylphenoxy)benzamide

HRID 1927749
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HRID 1927749 반응식
[Cl:1][C:2]1[CH:19]=[CH:18][C:5]([CH2:6][CH2:7][NH:8][C:9](=[O:17])[C:10]2[CH:15]=[CH:14][C:13]([OH:16])=[CH:12][CH:11]=2)=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].[Br:26][C:27]1[CH:28]=[C:29]([CH:32]=[CH:33][C:34]=1F)[CH:30]=[O:31]>CS(C)=O.C(OCC)(=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][CH2:7][NH:8][C:9](=[O:17])[C:10]2[CH:15]=[CH:14][C:13]([O:16][C:34]3[CH:33]=[CH:32][C:29]([CH:30]=[O:31])=[CH:28][C:27]=3[Br:26])=[CH:12][CH:11]=2)=[CH:18][CH:19]=1
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참가 물질

6

반응물 3

HCID 11430Potassium CarbonateHCID 1736043-Bromo-4-fluorobenzaldehydeHCID 60628097N-(4-chlorophenethyl)-4-hydroxybenzamide

생성물 1

HCID 86643286N-(4-chlorophenethyl)-4-(2-bromo-4-formylphenoxy)benzamide수율 71.2%

시약·촉매·용매 2

HCID 679Dimethyl Sulfoxide용매
HCID 8857
Ethyl Acetate
용매
2회

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온도
85 °C

실험 절차

N-(4-chlorophenethyl)-4-hydroxybenzamide (1.5 g, 5.4 mmol) was diluted with DMSO (15 mL) followed by the addition of K2CO3 (0.89 g, 6.4 mmol) and 3-bromo-4-fluorobenzaldehyde (1.0 g, 4.9 mmol). The reaction was stirred at 85° C. overnight and then cooled to ambient temperature. The reaction mixture was diluted with ethyl acetate and washed with twice with 10% sodium carbonate, water and brine, and then concentrated. The crude material was purified by silica gel chromatography eluting with hexanes:ethyl acetate (1:1) and then 100% ethyl acetate to yield N-(4-chlorophenethyl)-4-(2-bromo-4-formylphenoxy)benzamide (1.6 g, 71% yield).

후처리

  1. temperaturecooled to ambient temperature
  2. washwashed with twice with 10% sodium carbonate, water and brine
  3. concentrationconcentrated
  4. customThe crude material was purified by silica gel chromatography
  5. washeluting with hexanes:ethyl acetate (1:1)

출처 및 근거

ORD 기록
ord-1e7baa39cdbb4a42af63da61f22773e1
출처 데이터셋
uspto-grants-2012_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08183289B2

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