Triphenylphosphine → [1,1'-Biphenyl]-4-amine, 3-nitro-

HRID 617200

반응식

HRID 617200 반응식
Br[C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[C:4]([N+:9]([O-:11])=[O:10])[CH:3]=1.C([Sn](CCCC)(CCCC)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)CCC.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>CN(C=O)C.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.Cl[Pd]Cl>[C:17]1([C:2]2[CH:8]=[CH:7][C:5]([NH2:6])=[C:4]([N+:9]([O-:11])=[O:10])[CH:3]=2)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

참가 물질

6

반응물 3

HCID 11776TriphenylphosphineHCID 701324-Bromo-2-nitroanilineHCID 607632Tributylphenyltin

생성물 1

HCID 77705[1,1'-Biphenyl]-4-amine, 3-nitro-수율 75.2%

시약·촉매·용매 2

HCID 6102075Dichlorobis(triphenylphosphine)palladium촉매HCID 6228Dimethylformamide용매

실험 절차

A solution of 4-bromo-2-nitroaniline 17 (1.0 g, 4.67 mmol), tributylphenyl tin (2.2 g, 6.07 mmol), bis(triphenylphosphine)palladium (II) chloride (164 mg, 0.234 mmol), and triphenylphosphine (613 mg, 2.34 mmol) in DMF (15 ml) was heated under N2 at 120° C. overnight. After the solution was cooled to room temperature, the reaction mixture was directly chromatographed on silica gel eluting with 2-5% EtOAc/Hexane to give 752 mg (75%) of 5 as a yellow solid: mp 169-171° C.; IR (CHCl3) 3517, 3398, 3022, 1635, 1525, 1250; 1H NMR δ 8.38 (1H, d, J=2.2), 7.66 (1H, dd, J=8.7, 2.2), 7.59-7.54 (2H, m), 7.49-7.34 (3H, m), 6.90 (1H, d, J=8.8), 6.13 (NH, brs); 13C NMR δ 144.2, 139.3, 135.0, 130.9, 129.5, 127.8, 126.8. 124.4, 119.8, 112.8; Anal. Calcd for C12H10N2O2 : C, 67.28; H, 4.70; N, 13.08. Found: C, 67.38, H, 4.76; N, 13.01.

후처리

  1. customthe reaction mixture was directly chromatographed on silica gel eluting with 2-5% EtOAc/Hexane

출처 및 근거

ORD 기록
ord-dbeb5e97e690414f820cb6ba3948b5b6
출처 데이터셋
uspto-grants-1999_09
특허 번호
US05948797

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