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Sodium Carbonate → Methyl 2-methoxy-2'-methylbiphenyl-4-carboxylate

HRID 1249970
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HRID 1249970 반응식
[CH3:1][O:2][C:3](=[O:20])[C:4]1[CH:9]=[CH:8][C:7](OS(C(F)(F)F)(=O)=O)=[C:6]([O:18][CH3:19])[CH:5]=1.[CH3:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1OB(O)O.[Cl-].[Li+].C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC=CC=1.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:20])[C:4]1[CH:9]=[CH:8][C:7]([C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=2[CH3:21])=[C:6]([O:18][CH3:19])[CH:5]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

8

반응물 4

HCID 10340Sodium CarbonateHCID 433294Lithium ChlorideHCID 106151343-Methoxy-4-trifluoromethylsulfonyloxybenzoic acid methyl esterHCID 13862916Tolylboric acid

생성물 1

HCID 53941402Methyl 2-methoxy-2'-methylbiphenyl-4-carboxylate수율 99.8%

시약·촉매·용매 3

HCID 178418397
HCID 178418397, 화합물
촉매
HCID 962Water용매
HCID 1140Toluene용매

실험 절차

To a solution of 3-methoxy-4-trifluoromethylsulfonyloxybenzoic acid methyl ester (5 g) in toluene (200 ml) is added tetrakis(triphenylphosphine)palladium (0.9 g) under argon atmosphere, and the mixture is stirred at room temperature for five minutes. To the mixture are added (2-methylphenyl)boric acid (3.2 g), lithium chloride (1.01 g) and a 2M aqueous sodium carbonate solution (11.9 ml), and the mixture is stirred at 100° C. for two hours. To the mixture is added water, and the mixture is filtered through celite to remove the palladium. The filtrate is extracted with diethyl ether, and the ether layer is washed with water, dried, and evaporated. The residue is purified by silica gel column chromatography (solvent; n-hexane→ethyl acetate:n-hexane=1:10) to give 3-methoxy-4-(2-methylphenyl)benzoic acid methyl ester (4.07 g) as oil.

후처리

  1. filtrationthe mixture is filtered through celite
  2. customto remove the palladium
  3. extractionThe filtrate is extracted with diethyl ether
  4. washthe ether layer is washed with water
  5. customdried
  6. customevaporated
  7. customThe residue is purified by silica gel column chromatography (solvent; n-hexane→ethyl acetate:n-hexane=1:10)

출처 및 근거

ORD 기록
ord-4725c56417c048608b95ebd79129b7e0
출처 데이터셋
uspto-grants-2002_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06335327B1

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