Boron tribromide → 7-Bromo-4-(2-chlorophenyl)-9-hydroxy-1H-[1]benzofuro[3,2-e]isoindole-1,3(2H)-dione

HRID 11154Notes

Reaction equation

HRID 11154 reaction equation
[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]C)[CH:3]=1.B(Br)(Br)Br>>[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]([OH:27])[CH:3]=1

Participants

3

Reactant 2

HCID 25134Boron tribromideHCID 219803477-Bromo-4-(2-chlorophenyl)-9-methoxy-1H-[1]benzofuro[3,2-e]isoindole-1,3(2H)-dione

Product 1

HCID 219804697-Bromo-4-(2-chlorophenyl)-9-hydroxy-1H-[1]benzofuro[3,2-e]isoindole-1,3(2H)-dioneYield 98%

Procedure

Demethylation of (861) prepared as described in example 442 with BBr3 using the procedure described in example 80 gave (862) (98%) which was used without further purification. 1H NMR δ [(CD3)2SO] 8.04 (d, J=2.3 Hz, 1H), 7.91 (s, 1H), 7.56 (d, J=8 Hz, 1H), 7.45 (m, 3H), 7.2 (d, J=2.5 Hz, 1H). MH−:443.9, 441.9, 439.9.

Sources & evidence

ORD record
ord-792bed4399df4e62adb87dcc88912b45
Source dataset
uspto-grants-2006_08
Patent number
US07094798B1

Reaction notes

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