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Cesium fluoride → 5-Chloro-4-methoxy-4'-trifluoromethyl-biphenyl-3-carboxylic acid methyl ester

HRID 2373814
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인쇄 미리보기

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HRID 2373814 반응식
[F:1][C:2]([F:13])([F:12])[C:3]1[CH:8]=[CH:7][C:6](B(O)O)=[CH:5][CH:4]=1.[CH3:14][O:15][C:16](=[O:27])[C:17]1[CH:22]=[C:21](Br)[CH:20]=[C:19]([Cl:24])[C:18]=1[O:25][CH3:26].[F-].[Cs+]>COCCOC.CCOC(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>[CH3:14][O:15][C:16]([C:17]1[CH:22]=[C:21]([C:6]2[CH:7]=[CH:8][C:3]([C:2]([F:13])([F:12])[F:1])=[CH:4][CH:5]=2)[CH:20]=[C:19]([Cl:24])[C:18]=1[O:25][CH3:26])=[O:27]
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참가 물질

7

반응물 3

HCID 25953Cesium fluorideHCID 27343894-(Trifluoromethyl)phenylboronic acidHCID 11346502Methyl 5-bromo-3-chloro-2-methoxybenzoate

생성물 1

HCID 692071845-Chloro-4-methoxy-4'-trifluoromethyl-biphenyl-3-carboxylic acid methyl ester수율 76.4%

시약·촉매·용매 3

HCID 178418397HCID 178418397, 화합물
촉매
HCID 80711,2-Dimethoxyethane용매
HCID 8857Ethyl Acetate용매

반응 조건

온도
85 °C

실험 절차

4-Trifluoromethylphenylboronic acid (0.815 g, 4.29 mmol) was added to a solution of 5-Bromo-3-chloro-2-methoxy-benzoic acid methyl ester (1.0 g, 3.57 mmol), Pd(PPh3)4 (0.2 g, 0.178 mmol) and CsF (1.08 g, 7.15 mmol) in DME (10 mL ) and heated at 85° C. for 10 h. The reaction was diluted with EtOAc (20 mL) and filtered, filtrate was washed water, brine and dried over Na2SO4. Solvent was removed under reduced pressure and the silicagel column chromatography gave pure 5-Chloro-4-methoxy-4′-trifluoromethyl-biphenyl-3-carboxylic acid methyl ester (0.94 g).

후처리

  1. filtrationfiltered
  2. washfiltrate was washed water, brine
  3. dry with materialdried over Na2SO4
  4. customSolvent was removed under reduced pressure

출처 및 근거

ORD 기록
ord-e88e7ec2290d45b9816d91f42f94d7bf
출처 데이터셋
uspto-grants-2008_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07459472B2

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