Bromine → N-[4-(2-bromobutanoyl)phenyl]acetamide

HRID 1894747

反応式

HRID 1894747 の反応式
[C:1]([C:6]1[CH:11]=[CH:10][C:9]([NH:12][C:13](=[O:15])[CH3:14])=[CH:8][CH:7]=1)(=[O:5])[CH2:2][CH2:3][CH3:4].[Al+3].[Cl-].[Cl-].[Cl-].[Br:20]Br>C(Cl)Cl>[Br:20][CH:2]([CH2:3][CH3:4])[C:1]([C:6]1[CH:11]=[CH:10][C:9]([NH:12][C:13](=[O:15])[CH3:14])=[CH:8][CH:7]=1)=[O:5]

参加物

5

反応物 3

HCID 24408BromineHCID 4304236N-(4-Butyrylphenyl)acetamideHCID 6451240Aluminum(III) Chloride

生成物 1

HCID 63386157N-[4-(2-bromobutanoyl)phenyl]acetamide

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

A solution of N-(4-butyryl-phenyl)acetamide (3.47 g, 16.9 mmol) in 100 mL of anhydrous DCM was cooled to 0° C. under N2 and treated with AlCl3 (180 mg, 1.35 mmol). Approximately 10 mL of Br2 was added and the mixture was stirred for 10 min. The reactor was removed from the cooling bath and the remaining Br2 was added dropwise via syringe over 5 min. After 3 hr, the dark orange color of Br2 had faded and by 3¼ hr a precipitate had formed. The reaction was quenched with saturated NaHCO3. The phases were separated and the aqueous phase extracted three times with DCM. The combined extracts were dried over Na2SO4, filtered through a Celite® pad and concentrated in vacuo to give N-(4-(2-bromobutanoyl)phenyl)acetamide which was used without purification. MS ESI: m/z 284.10 [M+].

後処理

  1. customThe reactor was removed from the cooling bath
  2. additionthe remaining Br2 was added dropwise via syringe over 5 min
  3. waitAfter 3 hr
  4. waitthe dark orange color of Br2 had faded and by 3¼ hr
  5. customa precipitate had formed
  6. customThe reaction was quenched with saturated NaHCO3
  7. customThe phases were separated
  8. extractionthe aqueous phase extracted three times with DCM
  9. dry with materialThe combined extracts were dried over Na2SO4
  10. filtrationfiltered through a Celite® pad
  11. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-59a7b17f990e4d9694d8c8a2fa1f0f9b
出典データセット
uspto-grants-2013_08
特許番号
US08513291B2

関連ノート

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