Hydrochloric Acid → 3-Chloro-7-nitro-1-benzothiophene-5,6-diol

HRID 1881169Notes

Reaction equation

HRID 1881169 reaction equation
[Cl:1][C:2]1[C:3]2[CH:10]=[C:9]([O:11]C)[C:8]([OH:13])=[C:7]([N+:14]([O-:16])=[O:15])[C:4]=2[S:5][CH:6]=1.[Cl-].[Cl-].[Cl-].[Al+3].Cl>N1C=CC=CC=1>[Cl:1][C:2]1[C:3]2[CH:10]=[C:9]([OH:11])[C:8]([OH:13])=[C:7]([N+:14]([O-:16])=[O:15])[C:4]=2[S:5][CH:6]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 6451240Aluminum(III) ChlorideHCID 67094267HCID 67094267, compound

Product 1

HCID 159829743-Chloro-7-nitro-1-benzothiophene-5,6-diol

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
90 °C

Procedure

To the solution of 3-chloro-6-hydroxy-5-methoxy-7-nitro-benzo[b]thiophene (0.13 g) and pyridine (3.3 ml) was gradually added aluminum trichloride (0.09 g). The reaction mixture was heated at 90° C. for 2 hours. To the warm reaction (60° C.) mixture was added the mixture of ice and concentrated hydrochloric acid (1:1). The product was filtered, washed with 1M hydrochloric acid and water and dried under vacuum.

Workup

  1. customTo the warm reaction (60° C.) mixture
  2. additionwas added
  3. filtrationThe product was filtered
  4. washwashed with 1M hydrochloric acid and water
  5. customdried under vacuum

Sources & evidence

ORD record
ord-5f4ea3fefe3c491e918936cb3224cb12
Source dataset
uspto-grants-2012_11
Patent number
US08318785B2

Reaction notes

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