Sodium Carbonate → Ethyl 2'-methyl[1,1'-biphenyl]-3-carboxylate

HRID 719723

反応式

HRID 719723 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.C1(C)C=CC=CC=1B(O)O.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]=[CH:16][C:17]=2[CH3:20])[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 27332672-Methylphenyl boronic acidHCID 107287544'-Methyl-biphenyl-3-carboxylic acid ethyl ester

生成物 1

HCID 12853045Ethyl 2'-methyl[1,1'-biphenyl]-3-carboxylate

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

2′-Methyl-biphenyl-3-carboxylic acid ethyl ester was synthesized as described for 4′-methyl-biphenyl-3-carboxylic acid ethyl ester. Ethyl 3-bromobenzoate (8.02 g, 35.03 mmol, 1 eq.) and o-tolylboronic acid (5.0 g, 36.78 mmol, 1.05 eq.) in THF were treated with aqueous 2M sodium carbonate (38.5 mL, 77.07 mmol, 2.2 eq.), palladium(II) acetate (0.79 g, 3.50 mmol, 10 mol %), triphenylphosphine (4.04 g, 15.40 mmol, 4.4×Pd), and copper(I) iodide (0.22 g, catalyst). When complete, the reaction was worked up as described leaving a dark brown oil.

後処理

  1. customas described leaving a dark brown oil

出典と根拠

ORDレコード
ord-bd5da445a8064ef199454b371e0862a1
出典データセット
uspto-grants-2006_11
特許番号
US07132456B2

関連ノート

読み込み中…