1-Bromo-2-Chloroethane → 3'-[(2-Bromoethyl)oxy]-4-biphenylcarboxamide

HRID 471790ノート

反応式

HRID 471790 の反応式
[OH:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:13]=[CH:12][C:11]([C:14]([NH2:16])=[O:15])=[CH:10][CH:9]=2)[CH:5]=[CH:6][CH:7]=1.[Br:17][CH2:18][CH2:19][Cl:20].C(=O)([O-])[O-].[K+].[K+]>C(O)C.O.C(OCC)(=O)C>[Cl:20][CH2:19][CH2:18][O:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:13]=[CH:12][C:11]([C:14]([NH2:16])=[O:15])=[CH:10][CH:9]=2)[CH:5]=[CH:6][CH:7]=1.[Br:17][CH2:18][CH2:19][O:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:13]=[CH:12][C:11]([C:14]([NH2:16])=[O:15])=[CH:10][CH:9]=2)[CH:5]=[CH:6][CH:7]=1

参加物

8

反応物 3

HCID 78491-Bromo-2-ChloroethaneHCID 11430Potassium CarbonateHCID 582763863'-Hydroxy-[1,1'-biphenyl]-4-carboxamide

生成物 2

HCID 582762623'-[(2-Bromoethyl)oxy]-4-biphenylcarboxamideHCID 582763523'-[(2-Chloroethyl)oxy]-4-biphenylcarboxamide

試薬・触媒・溶媒 3

HCID 702Ethanol溶媒HCID 962Water溶媒2 回HCID 8857Ethyl Acetate溶媒

実験手順

Into three separate microwave vials was distributed equally a mixture of 3′-hydroxy-4-biphenylcarboxamide (Intermediate A-1-1) (1.0 g, 0.005 mol), 1-bromo-2-chloroethane (2.8 g, 0.02 mol) and potassium carbonate (2.8 g, 0.02 mol) in ethanol (2.2 mL) and water (1.8 mL) was placed in a microwave at 150° C. until the reaction was complete as determined by LC/MS. The contents of the vials were combined and diluted with ethyl acetate and water. The aqueous phase was extracted with ethyl acetate. The combined organic phase was dried (Na2SO4), filtered and concentrated in vacuo to give 3′-[(2-chloroethyl)oxy]-4-biphenylcarboxamide and 3′-[(2-bromoethyl)oxy]-4-biphenylcarboxamide as an off-white solid. LC/MS indicates that this product is a mixture of the chloroethoxy (M+H) 276, 2.34 min. (LC/MS method A) and the bromoethoxy (M+H) 320, tR 2.42 min. in a ratio of ˜81/19% respectively. This product was used without further purification.

後処理

  1. customInto three separate microwave vials
  2. customwas placed in a microwave at 150° C. until the reaction
  3. extractionThe aqueous phase was extracted with ethyl acetate
  4. dry with materialThe combined organic phase was dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-d65534616d0249ba92534e89944578f2
出典データセット
uspto-grants-2014_01
特許番号
US08633175B2

反応ノート

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