Hydrogen Bromide → 5,6-Dihydroxy-7-nitro-1-benzothiophene-2-carboxylic acid

HRID 1881189Notes

Reaction equation

HRID 1881189 reaction equation
C[O:2][C:3]([C:5]1[S:9][C:8]2[C:10]([N+:20]([O-:22])=[O:21])=[C:11]([O:17]CC)[C:12]([O:14]CC)=[CH:13][C:7]=2[CH:6]=1)=[O:4].Br>C(O)(=O)C>[OH:14][C:12]1[C:11]([OH:17])=[C:10]([N+:20]([O-:22])=[O:21])[C:8]2[S:9][C:5]([C:3]([OH:4])=[O:2])=[CH:6][C:7]=2[CH:13]=1

Participants

4

Reactant 2

HCID 260Hydrogen BromideHCID 67094308HCID 67094308, compound

Product 1

HCID 159831045,6-Dihydroxy-7-nitro-1-benzothiophene-2-carboxylic acid

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

5,6-Diethoxy-7-nitro-benzo[b]thiophene-2-carboxylic acid methyl ester (160 mg), hydrobromic acid (8 ml) and acetic acid (8 ml) was refluxed for 6 hours and stirred at room temperature overnight. The solid was filtered and washed with a solution of acetic acid and hydrobromic acid (1:1) and water. The product was recrystallized from acetonitrile.

Workup

  1. filtrationThe solid was filtered
  2. washwashed with a solution of acetic acid and hydrobromic acid (1:1) and water
  3. customThe product was recrystallized from acetonitrile

Sources & evidence

ORD record
ord-00f803d5dd974fc296bd3729dd3baaea
Source dataset
uspto-grants-2012_11
Patent number
US08318785B2

Reaction notes

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