Hydrogen Bromide → 2,1,3-Benzothiadiazol-5-ol

HRID 899387Notes

Reaction equation

HRID 899387 reaction equation
C[O:2][C:3]1[CH:11]=[CH:10][C:6]2=[N:7][S:8][N:9]=[C:5]2[CH:4]=1.Br>>[N:7]1[S:8][N:9]=[C:5]2[CH:4]=[C:3]([OH:2])[CH:11]=[CH:10][C:6]=12

Participants

3

Reactant 2

HCID 260Hydrogen BromideHCID 27812455-Methoxy-2,1,3-benzothiadiazole

Product 1

HCID 27718862,1,3-Benzothiadiazol-5-olYield 27%

Conditions

Temperature
10 °C

Procedure

5-Methoxy-benzo-[2,1,3]-thiadiazole (4.09 g, 24.6 mmol) was stirred with hydrobromic acid (60 ml, 165 mmol, 30% in acetic acid) at 80° C. for 5 days. The mixture was cooled to 10° C. and filtered. The solids were purified by short column chromatography (50% ethyl acetate/hexane). Solvents were stripped in vacuo to afford 1.0 g of a yellow solid (27% yield).

Workup

  1. filtrationfiltered
  2. customThe solids were purified by short column chromatography (50% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-93f18af351de42168a5a403522aaabb9
Source dataset
uspto-grants-2008_04
Patent number
US07354941B2

Reaction notes

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