Dichloromethane → (2'-Formyl-6-methoxy-4'-trifluoromethyl-biphenyl-3-yl)-acetic acid methyl ester

HRID 38703

反応式

HRID 38703 の反応式
[CH3:1][O:2][C:3](=[O:22])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([O:11][CH3:12])=[C:7](B2OC(C)(C)C(C)(C)O2)[CH:6]=1.Br[C:24]1[CH:31]=[CH:30][C:29]([C:32]([F:35])([F:34])[F:33])=[CH:28][C:25]=1[CH:26]=[O:27].C(=O)([O-])[O-].[K+].[K+].C(Cl)Cl>COCCOC.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.O>[CH3:1][O:2][C:3](=[O:22])[CH2:4][C:5]1[CH:6]=[C:7]([C:24]2[CH:31]=[CH:30][C:29]([C:32]([F:35])([F:34])[F:33])=[CH:28][C:25]=2[CH:26]=[O:27])[C:8]([O:11][CH3:12])=[CH:9][CH:10]=1

参加物

8

反応物 4

HCID 6344DichloromethaneHCID 11430Potassium CarbonateHCID 70180472-Bromo-5-(trifluoromethyl)benzaldehydeHCID 57576289Methyl 2-(4-methoxy-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-YL)phenyl)acetate

生成物 1

HCID 86633167(2'-Formyl-6-methoxy-4'-trifluoromethyl-biphenyl-3-yl)-acetic acid methyl ester

試薬・触媒・溶媒 3

HCID 178418397HCID 178418397、化合物触媒HCID 962Water溶媒HCID 80711,2-Dimethoxyethane溶媒

反応条件

温度
90 °C

実験手順

[4-Methoxy-3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-acetic acid methyl ester (4.99 g, 16.4 mmol), 2-bromo-5-trifluoromethyl-benzaldehyde (4.15 g, 16.4 mmol), and potassium carbonate (5.67 g, 41.0 mmol) were combined in DME (40 mL) and H2O (20 mL), and the mixture was purged with N2 for 30 minutes. Tetrakis(triphenylphosphine)palladium(0) (1.90 g, 1.64 mmol) was added, and the reaction was stirred at 90° C. for 10 hours. The mixture was worked-up with CH2Cl2 and H2O, and the organic layer was dried over MgSO4, filtered, and concentrated. The residue was purified by silica gel chromatography to give the title compound.

後処理

  1. customH2O (20 mL), and the mixture was purged with N2 for 30 minutes
  2. dry with materialthe organic layer was dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was purified by silica gel chromatography

出典と根拠

ORDレコード
ord-798993da5a854441b8f77ec2812121f9
出典データセット
uspto-grants-2013_09
特許番号
US08524748B2

関連ノート

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