Ethyl Acetate → 7-bromo-4-methyl-1H-indole

HRID 992473

반응식

HRID 992473 반응식
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][C:3]=1[N+:9]([O-])=O.[CH:12]([Mg]Br)=[CH2:13].[Cl-].[NH4+].C(OCC)(=O)C>O1CCCC1>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[C:4]2[C:3]=1[NH:9][CH:13]=[CH:12]2

참가 물질

6

반응물 4

HCID 8857Ethyl AcetateHCID 25517Ammonium ChlorideHCID 792244-Bromo-3-nitrotolueneHCID 178418507HCID 178418507, 화합물

생성물 1

HCID 187528627-bromo-4-methyl-1H-indole수율 56.1%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

To 300 ml of a solution of 65.0 g (301 mmol) of 2-bromo-5-methylnitrobenzene in tetrahydrofuran was added 1 liter of a 1.0M solution of vinyl magnesium bromide (1 mol) in tetrahydrofuran at −60° C. in a nitrogen atmosphere under stirring during 1 hour. To the reaction mixed solution were added a saturated aqueous solution of ammonium chloride and ethyl acetate, and the resulting insoluble matters were filtered off. The resulting filtrate was dried over magnesium sulfate, concentrated, and then the resulting residue was purified by a silica gel column chromatography to give 35.5 g of the title compound.

후처리

  1. additionTo the reaction mixed solution
  2. filtrationthe resulting insoluble matters were filtered off
  3. dry with materialThe resulting filtrate was dried over magnesium sulfate
  4. concentrationconcentrated
  5. customthe resulting residue was purified by a silica gel column chromatography

출처 및 근거

ORD 기록
ord-76224b96640b410aa0643868eb036fe9
출처 데이터셋
uspto-grants-2002_10
특허 번호
US06469043B1

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