Nitrogen → 2-Bromo-1-(4-methyl-3-nitrophenyl)ethan-1-one

HRID 539730

반응식

HRID 539730 반응식
[CH3:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](Cl)=[O:7])=[CH:4][C:3]=1[N+:11]([O-:13])=[O:12].[CH3:14][Si](C=[N+]=[N-])(C)C.[BrH:21].CC(O)=O.N#N>C(Cl)Cl>[Br:21][CH2:14][C:6]([C:5]1[CH:9]=[CH:10][C:2]([CH3:1])=[C:3]([N+:11]([O-:13])=[O:12])[CH:4]=1)=[O:7]

참가 물질

6

반응물 4

HCID 947NitrogenHCID 663234-Methyl-3-nitrobenzoyl chlorideHCID 167693TrimethylsilyldiazomethaneHCID 21893785Acetic Acid Mixture with Hydrobromic Acid

생성물 1

HCID 38004222-Bromo-1-(4-methyl-3-nitrophenyl)ethan-1-one수율 93.8%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a stirred solution of 4-methyl-3-nitrobenzoyl chloride (Sigma-Aldrich, 2.0 g, 10 mmol) in CH2Cl2 (50 mL) is added trimethylsilyldiazomethane (2.0 M in hexanes, 40 mmol). The mixture is stirred for 2 hours at room temp, then cooled to 0° C. and a solution of HBr/HOAc (6.33 mL, 33% of HBr in HOAc, 35 mmol) is added dropwise (N2 evolution). After addition the mixture is stirred at 0° C. for 5 minutes, concentrated and purified by silica gel chromatography (CH2Cl2) to give the title compound (2.42 g, 93% yield) as a light yellow solid: Rf 0.61 (CH2Cl2)

후처리

  1. temperaturecooled to 0° C.
  2. additionAfter addition the mixture
  3. stirringis stirred at 0° C. for 5 minutes
  4. concentrationconcentrated
  5. custompurified by silica gel chromatography (CH2Cl2)

출처 및 근거

ORD 기록
ord-d233ac288c324ac69bad3ac68f696d43
출처 데이터셋
uspto-grants-2014_10
특허 번호
US08871767B2

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