Reaktion #11249

ord-6037c376f6cf4a77b61b13054950d1d6

Reaktionsgleichung

COc1cc(Br)c2oc3c(c2c1)C1C(=O)NC(=O)C1C(c1ccccc1Cl)C3
( 860 )
COc1cc(Br)c2oc3c(c2c1)C1C(=O)NC(=O)C1C(c1ccccc1Cl)C3
7-Bromo-4-(2-chlorophenyl)-9-methoxy-3a,4,5,10c-tetrahydro-1H-[1]benzofuro[3,2-e]isoindole-1,3(2H)-dione
→
COc1cc(Br)c2oc3cc(-c4ccccc4Cl)c4c(c3c2c1)C(=O)NC4=O
dibenzofuran
Ausbeute 67.0%
COc1cc(Br)c2oc3cc(-c4ccccc4Cl)c4c(c3c2c1)C(=O)NC4=O
7-Bromo-4-(2-chlorophenyl)-9-methoxy-1H-[1]benzofuro[3,2-e]isoindole-1,3(2H)-dione
Ausbeute 67.0%

Edukte

COc1cc(Br)c2oc3c(c2c1)C1C(=O)NC(=O)C1C(c1ccccc1Cl)C3
( 860 )
COc1cc(Br)c2oc3c(c2c1)C1C(=O)NC(=O)C1C(c1ccccc1Cl)C3
7-Bromo-4-(2-chlorophenyl)-9-methoxy-3a,4,5,10c-tetrahydro-1H-[1]benzofuro[3,2-e]isoindole-1,3(2H)-dione

Reagenzien

[O]=[Mn]=[O]
MnO2

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Vorschrift

Aromatisation of (860) prepared as described in example442 with MnO2 using the procedure described in example 79 gave the dibenzofuran (861) as a yellow solid (67%). 1H NMR δ [(CD3)2SO] 8.22 (d, J=2.6 Hz, 1H), 8.14 (s, 1H), 7.62 (m, 2H), 7.48 (m, 3H), 3.98 (s, 3H). MH−:458,457,456,454.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US07094798B1uspto-grants-2006_08