Boron tribromide → HCID 135418181, compound

HRID 1824799Notes

Reaction equation

[C:1]([C:4]1[C:9]2[N:10]=[C:11]([C:13]3[CH:18]=[CH:17][C:16]([O:19]C)=[CH:15][CH:14]=3)[S:12][C:8]=2[CH:7]=[C:6]([O:21]C)[CH:5]=1)([OH:3])=[O:2].B(Br)(Br)Br>>[C:1]([C:4]1[C:9]2[N:10]=[C:11]([C:13]3[CH:18]=[CH:17][C:16]([OH:19])=[CH:15][CH:14]=3)[S:12][C:8]=2[CH:7]=[C:6]([OH:21])[CH:5]=1)([OH:3])=[O:2]

Participants

Reactant 2

HCID 25134Boron tribromide

HCID 22144527HCID 22144527, compound

Product 1

HCID 135418181HCID 135418181, compoundYield 74.4%

Procedure

4-Carboxy-6-methoxy-2-(4-methoxy-phenyl)-benzothiazole (50 mg, 0.159 mmol) was treated with boron tribromide under standard condition to give 4-carboxy-6-hydroxy-2-(4-hydroxy-phenyl)-benzothiazole (34 mg, 74% yield) as a yellow solid. Mass spec: MH+=288. 1H NMR (DMSO-d6): 10.24 (s, 1H), 10.16 (s, 1H), 7.91 (d, 2H), 7.67 (s, 1H), 7.48 (s, 1H), 6.95 (d, 2H).

Sources & evidence

ORD record: ord-74f6996c911d4383855fda0ef64b344c
Source dataset: uspto-grants-2006_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07045539B2

Reaction notes

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