7-Bromo-4-(2-chlorophenyl)-9-methoxy-3a,4,5,10c-tetrahydro-1H-[1]benzofuro[3,2-e]isoindole-1,3(2H)-dione → 7-Bromo-4-(2-chlorophenyl)-9-methoxy-1H-[1]benzofuro[3,2-e]isoindole-1,3(2H)-dione

HRID 11153Notes

Reaction equation

HRID 11153 reaction equation
[Br:1][C:2]1[C:7]2[O:8][C:9]3[CH2:17][CH:16]([C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=4[Cl:24])[CH:15]4[CH:11]([C:12](=[O:26])[NH:13][C:14]4=[O:25])[C:10]=3[C:6]=2[CH:5]=[C:4]([O:27][CH3:28])[CH:3]=1>O=[Mn]=O>[Br:1][C:2]1[C:7]2[O:8][C:9]3[CH:17]=[C:16]([C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=4[Cl:24])[C:15]4[C:14](=[O:25])[NH:13][C:12](=[O:26])[C:11]=4[C:10]=3[C:6]=2[CH:5]=[C:4]([O:27][CH3:28])[CH:3]=1

Participants

3

Reactant 1

HCID 219804897-Bromo-4-(2-chlorophenyl)-9-methoxy-3a,4,5,10c-tetrahydro-1H-[1]benzofuro[3,2-e]isoindole-1,3(2H)-dione

Product 1

HCID 219803477-Bromo-4-(2-chlorophenyl)-9-methoxy-1H-[1]benzofuro[3,2-e]isoindole-1,3(2H)-dioneYield 67%

Reagents, catalysts & solvents 1

HCID 14801Manganese dioxideCatalyst

Procedure

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.

Sources & evidence

ORD record
ord-6037c376f6cf4a77b61b13054950d1d6
Source dataset
uspto-grants-2006_08
Patent number
US07094798B1

Reaction notes

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