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Dichloromethane → 2-Aminobiphenyl

HRID 2181824
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HRID 2181824 반응식
I[C:2]1[CH:8]=[CH:7][CH:6]=[CH:5][C:3]=1[NH2:4].[CH3:9][O:10][C:11]1[CH:12]=[C:13](B(O)O)[CH:14]=[CH:15][CH:16]=1.ClCCl.[OH-].[Na+]>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[CH3:9][O:10][C:11]1[CH:16]=[C:15]([C:2]2[CH:8]=[CH:7][CH:6]=[CH:5][C:3]=2[NH2:4])[CH:14]=[CH:13][CH:12]=1.[C:2]1([C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:3]([NH2:4])=[CH:5][CH:6]=[CH:7][CH:8]=1
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7

반응물 4

HCID 6344DichloromethaneHCID 119952-IodoanilineHCID 14798Sodium HydroxideHCID 2734370(3-Methoxyphenyl)boronic acid

생성물 2

HCID 70152-Aminobiphenyl수율 197.5%HCID 2759560Sbb007488

시약·촉매·용매 1

HCID 44119782
Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)
촉매

실험 절차

3′-Methoxy-1,1′-biphenyl-2-ylamine was prepared from 2-iodoaniline (3.64 g, 16.7 mmol), 3-methoxyphenylboronic acid (2.54 g, 16.7 mmol), [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium (II) complex with dichloromethane (0.41 g, 0.50 mmol), and a 5 N aqueous sodium hydroxide solution (6.7 mL, 33.5 mmol), according to the procedure and in the same manner as described in Example 32, Method A, Step a, to afford the intermediate biphenyl amine as an oil (2.79 g, 84%). The title compound was prepared from the above intermediate biphenyl amine (0.75 g, 3.8 mmol), acetic anhydride (1.4 mL, 15 mmol), 4-(N,N-dimethylamino)pyridine (0.05 g, 0.4 mmol), and pyridine (1.2 mL, 15 mmol) according to the same procedure as described in Example 32, Method A, Step a to yield N-(3′-methoxy-1,1′-biphenyl-2-yl)acetamide as a solid (0.60 g, 66%), m.p. 105-107° C.;

출처 및 근거

ORD 기록
ord-a414dcfbe1214a2fb12e16cd15e45620
출처 데이터셋
uspto-grants-2005_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06894061B2

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