Sodium Carbonate → 3'-Methyl-biphenyl-3-carboxylic acid ethyl ester

HRID 719704

反応式

HRID 719704 の反応式
[CH2:1]([O:3][C:4]([C:6]1[CH:7]=[C:8]([C:12]2[CH:17]=[CH:16][C:15](C)=[CH:14][CH:13]=2)[CH:9]=[CH:10][CH:11]=1)=[O:5])[CH3:2].Br[C:20]1C=C(C=CC=1)C(OCC)=O.CC1C=C(B(O)O)C=CC=1.C(=O)([O-])[O-].[Na+].[Na+].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1COCC1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.[Cu]I>[CH2:1]([O:3][C:4]([C:6]1[CH:7]=[C:8]([C:12]2[CH:13]=[CH:14][CH:15]=[C:16]([CH3:20])[CH:17]=2)[CH:9]=[CH:10][CH:11]=1)=[O:5])[CH3:2]

参加物

9

反応物 5

HCID 10340Sodium CarbonateHCID 11776TriphenylphosphineHCID 90488Ethyl 3-bromobenzoateHCID 27339503-Tolylboronic acidHCID 107287544'-Methyl-biphenyl-3-carboxylic acid ethyl ester

生成物 1

HCID 586105893'-Methyl-biphenyl-3-carboxylic acid ethyl ester

試薬・触媒・溶媒 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 167845palladium(II) acetate触媒HCID 8028Tetrahydrofuran溶媒

実験手順

3′-Methyl-biphenyl-3-carboxylic acid ethyl ester was synthesized as described for 4′-methyl-biphenyl-3-carboxylic acid ethyl ester. Ethyl 3-bromobenzoate (3.83 g, 16.72 mmol, 1 eq.) and 3-methylbenzeneboronic acid (2.5 g, 18.39 mmol, 1.1 eq.) in THF were treated with aqueous sodium carbonate (2M solution, 18.4 mL, 36.78 mmol, 2.2 eq.), palladium(II) acetate (0.37 g, 1.67 mmol, 10 mol %), triphenylphosphine (1.93 g, 7.35 mmol, 4.4×Pd), and copper(I) iodide (0.1 g, catalyst). When complete, the reaction was worked up as described leaving a brown oil.

後処理

  1. customas described leaving a brown oil

出典と根拠

ORDレコード
ord-e65df2a6181a4dff925d97d874621ff9
出典データセット
uspto-grants-2006_11
特許番号
US07132456B2

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