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

HRID 478343
ノート
印刷プレビュー

反応式

HRID 478343 の反応式
[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
参加物実験手順後処理出典と根拠反応ノート

参加物

8

反応物 4

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

生成物 1

HCID 53941402Methyl 2-methoxy-2'-methylbiphenyl-4-carboxylate収率 99.8%

試薬・触媒・溶媒 3

HCID 178418397
HCID 178418397、化合物
触媒
HCID 962Water溶媒
HCID 1140Toluene溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-a827372b70b34b2d9037278f9c7ef180
出典データセット
uspto-grants-2003_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06642223B2

反応ノート

読み込み中…

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