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

HRID 1927749

反応式

HRID 1927749 の反応式
[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

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 679Dimethyl Sulfoxide溶媒HCID 8857Ethyl Acetate溶媒2 回

反応条件

温度
85 °C

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-1e7baa39cdbb4a42af63da61f22773e1
出典データセット
uspto-grants-2012_05
特許番号
US08183289B2

関連ノート

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