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

HRID 538863

반응식

HRID 538863 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

Step-2: 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 N, 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 0.5 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+].

후처리

  1. customThe reactor was removed from the cooling bath
  2. additionthe remaining Br2 was added dropwise via syringe over 0.5 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

출처 및 근거

ORD 기록
ord-77dad88af4bb4023a54fc9d7763877b5
출처 데이터셋
uspto-grants-2014_10
특허 번호
US08865752B2

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