Morpholine → 4-[4-(4-Iodo-phenoxy)-phenyl]-morpholine

HRID 2353260

Reaktionsgleichung

Reaktionsgleichung von HRID 2353260
I[C:2]1[CH:7]=[CH:6][C:5]([O:8][C:9]2[CH:14]=[CH:13][C:12]([I:15])=[CH:11][CH:10]=2)=[CH:4][CH:3]=1.[NH:16]1[CH2:21][CH2:20][O:19][CH2:18][CH2:17]1.P(C(C)(C)C)(C(C)(C)C)C(C)(C)C.O(C(C)(C)C)[Na]>C1(C)C=CC=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[I:15][C:12]1[CH:13]=[CH:14][C:9]([O:8][C:5]2[CH:6]=[CH:7][C:2]([N:16]3[CH2:21][CH2:20][O:19][CH2:18][CH2:17]3)=[CH:3][CH:4]=2)=[CH:10][CH:11]=1

Komponenten

7

Edukt 4

HCID 8083MorpholineHCID 343601,1'-Oxybis(4-iodobenzene)HCID 83681Tris(1,1-dimethylethyl)phosphineHCID 178418730sodium 2-methylpropan-2-olate

Produkt 1

HCID 236277884-[4-(4-Iodo-phenoxy)-phenyl]-morpholineAusbeute 99 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 9811564Bis(dibenzylideneacetone)palladiumKatalysatorHCID 1140TolueneLösungsmittel

Versuchsvorschrift

The title compound (0.36 g, 99%) was prepared from 4-iodopheyl ether (0.42 g, 1 mmol) and morpholine (0.087 g, 1 mmol) in the presence of Pd2(dba)3 (0.027 g, 0.03 mmol), PtBu3 (0.058 g. 0.28 mmol) and NaO-t-Bu (0.095 g, 1 mmol) in toluene by using the procedure described in step 1 of Example 17: MS (ESI) m/z 382 (M+H); 1H NMR (400 MHz, CDCl3) δ 3.12 (t, J=4.8, 4H), 3.87 (t, J=4.8 Hz, 4H), 6.69-6.72 (m, 2H), 6.89-6.92 (m, 4H), 7.55-7.57 (m, 2H).

Quellen und Nachweise

ORD-Eintrag
ord-d338b8ca4dc44c5c8f99637785b18744
Quelldatensatz
uspto-grants-2010_07
Patentnummer
US07750012B2

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