Acetic Acid → 5-hydroxybenzo[b]thiophene-2-carboxylic acid

HRID 1872373Notes

Reaction equation

HRID 1872373 reaction equation
[C:1]([C:4]1[S:8][C:7]2[CH:9]=[CH:10][C:11]([O:13]C)=[CH:12][C:6]=2[CH:5]=1)(=[O:3])N.Br.C(O)(=[O:18])C>>[OH:13][C:11]1[CH:10]=[CH:9][C:7]2[S:8][C:4]([C:1]([OH:3])=[O:18])=[CH:5][C:6]=2[CH:12]=1

Participants

4

Reactant 3

HCID 176Acetic AcidHCID 260Hydrogen BromideHCID 21182275HCID 21182275, compound

Product 1

HCID 2686515-hydroxybenzo[b]thiophene-2-carboxylic acid

Conditions

Temperature
110 °C

Procedure

A mixture of 2-Carbamoyl-5-methoxybenzo[b]thiophene (2.0 g), acetic acid (5 ml) and 48% hydrobromic acid (20 ml) was stirred for 16 hours at 110° C., and the mixture was poured into the ice-water. The resulting precipitate was collected by filtration, and dried to give 5-Hydroxybenzo[b]thiophene-2-carboxylic acid (1.66 g).

Workup

  1. filtrationThe resulting precipitate was collected by filtration
  2. customdried

Sources & evidence

ORD record
ord-9368ac8bb7f243bbb943db3cb24b76cf
Source dataset
uspto-grants-2000_08
Patent number
US06107458

Reaction notes

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