Methyl 2-bromobenzoate → Methyl 2-(4-formylphenyl)benzoate

HRID 1594187노트

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HRID 1594187 반응식
[CH:1]([C:3]1[CH:8]=[CH:7][C:6](OB(O)O)=[CH:5][CH:4]=1)=[O:2].[CH3:13][O:14][C:15](=[O:23])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1Br.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>CN(C)C=O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:13][O:14][C:15](=[O:23])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[C:6]1[CH:7]=[CH:8][C:3]([CH:1]=[O:2])=[CH:4][CH:5]=1

참가 물질

6

반응물 3

HCID 11894Methyl 2-bromobenzoateHCID 62657Potassium Phosphate, TribasicHCID 21940015p-Formylphenylboric acid

생성물 1

HCID 4325150Methyl 2-(4-formylphenyl)benzoate수율 56.5%

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매HCID 6228Dimethylformamide용매

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온도
75 °C

실험 절차

To a solution of 4-formylphenylboric acid (6.7 g) in N,N-dimethylformamide (100 ml) were added 2-bromobenzoic acid methyl ester (6.5 g), tetrakis(triphenylphosphine)palladium [Pd(PPh3)4] (1.0 g) and tripotassium phosphate (23 g). The reaction mixture was stirred for 5 hours at 75° C. The reaction mixture was filtrated and concentrated. To the residue were added 1N hydrochloric acid and ethyl acetate, and the mixture was concentrated. The residue was purified by column chromatography on silica gel (hexane:ethyl acetate=9:1) to give the title compound (4.1 g) having the following physical data.

후처리

  1. filtrationThe reaction mixture was filtrated
  2. concentrationconcentrated
  3. additionTo the residue were added 1N hydrochloric acid and ethyl acetate
  4. concentrationthe mixture was concentrated
  5. customThe residue was purified by column chromatography on silica gel (hexane:ethyl acetate=9:1)

출처 및 근거

ORD 기록
ord-06d6b051a5e24121b349c0301dee4eec
출처 데이터셋
uspto-grants-2007_11
특허 번호
US07300917B2

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