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

HRID 719723

반응식

HRID 719723 반응식
[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]

참가 물질

9

반응물 5

HCID 10340Sodium CarbonateHCID 11776TriphenylphosphineHCID 90488Ethyl 3-bromobenzoateHCID 27332672-Methylphenyl boronic acidHCID 107287544'-Methyl-biphenyl-3-carboxylic acid ethyl ester

생성물 1

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

시약·촉매·용매 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 167845palladium(II) acetate촉매HCID 8028Tetrahydrofuran용매

실험 절차

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.

후처리

  1. customas described leaving a dark brown oil

출처 및 근거

ORD 기록
ord-bd5da445a8064ef199454b371e0862a1
출처 데이터셋
uspto-grants-2006_11
특허 번호
US07132456B2

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