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

HRID 350969Notes

Reaction equation

HRID 350969 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-Methoxybenzo-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. 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. custom5 days
  2. filtrationfiltered
  3. customThe solids were purified by short column chromatography (50% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-b759e3fd096242bea2c8a234db919876
Source dataset
uspto-grants-2007_02
Patent number
US07183293B2

Reaction notes

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