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

HRID 38703

반응식

HRID 38703 반응식
[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

참가 물질

8

반응물 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

생성물 1

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

시약·촉매·용매 3

HCID 178418397HCID 178418397, 화합물촉매HCID 962Water용매HCID 80711,2-Dimethoxyethane용매

반응 조건

온도
90 °C

실험 절차

[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.

후처리

  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

출처 및 근거

ORD 기록
ord-798993da5a854441b8f77ec2812121f9
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08524748B2

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