Boron tribromide → 4-(2-Chlorophenyl)-9-hydroxy-1H-[1]benzothieno[3,2-e]isoindole-1,3(2H)-dione

HRID 11138Notes

Reaction equation

HRID 11138 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:16]2[C:15](=[O:17])[NH:14][C:13](=[O:18])[C:12]=2[C:11]2[C:19]3[CH:25]=[C:24]([O:26]C)[CH:23]=[CH:22][C:20]=3[S:21][C:10]=2[CH:9]=1.B(Br)(Br)Br>>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:16]2[C:15](=[O:17])[NH:14][C:13](=[O:18])[C:12]=2[C:11]2[C:19]3[CH:25]=[C:24]([OH:26])[CH:23]=[CH:22][C:20]=3[S:21][C:10]=2[CH:9]=1

Participants

3

Reactant 2

HCID 25134Boron tribromideHCID 219808514-(2-Chlorophenyl)-9-methoxy-1H-[1]benzothieno[3,2-e]isoindole-1,3(2H)-dione

Product 1

HCID 219806964-(2-Chlorophenyl)-9-hydroxy-1H-[1]benzothieno[3,2-e]isoindole-1,3(2H)-dioneYield 65%

Procedure

Demethylation of (839) prepared as described in example 374 with BBr3 using the procedure described in example 80 except that the reaction time was 48 h gave (840) (65%) as a yellow solid, mp 311–313° C. 1H NMR δ [(CD3)2SO] 11.42 (s, 1H), 9.85 (s, 1H), 9.17 (d, J=2.5 Hz, 1H), 8.32 (s, 1H), 7.9 (d, J=9 Hz, 1H), 7.62 (m, 2H), 7.5 (m, 3H), 7.17 (dd, J=2.5, 9 Hz, 1H). MH+346. Found C, 68.75; H, 3.43; N, 3.89; S, 9.35. C20H11NO3S.0.2H2O requires: C, 68.83; H, 3.29; N, 4.01; S, 9.19.

Sources & evidence

ORD record
ord-0431b74d082947e191c50707609c9568
Source dataset
uspto-grants-2006_08
Patent number
US07094798B1

Reaction notes

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