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

HRID 1594187ノート

反応式

HRID 1594187 の反応式
[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

参加物

6

反応物 3

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

生成物 1

HCID 4325150Methyl 2-(4-formylphenyl)benzoate収率 56.5%

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒HCID 6228Dimethylformamide溶媒

反応条件

温度
75 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-06d6b051a5e24121b349c0301dee4eec
出典データセット
uspto-grants-2007_11
特許番号
US07300917B2

反応ノート

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