Sodium Hydroxide → 5-Iodo-1-benzothiophene-2-carboxylic acid

HRID 2288059Notes

Reaction equation

HRID 2288059 reaction equation
[OH-].[Na+].[I:3][C:4]1[CH:17]=[CH:16][C:7]2[S:8][C:9]([C:11]([O:13]CC)=[O:12])=[CH:10][C:6]=2[CH:5]=1>O.C(O)C>[I:3][C:4]1[CH:17]=[CH:16][C:7]2[S:8][C:9]([C:11]([OH:13])=[O:12])=[CH:10][C:6]=2[CH:5]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 12094044Ethyl 5-iodobenzo[b]thiophene-2-carboxylate

Product 1

HCID 187029605-Iodo-1-benzothiophene-2-carboxylic acidYield 91.3%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

Sodium hydroxide (5 g) in water (150 ml) was added to ethyl 5-iodobenzo[b]thiophene-2-carboxylate (14 g) in ethanol (200 ml) and the mixture was stirred for 16 hours. The mixture was concentrated to about 150 ml by evaporation and the mixture was adjusted to ~pH 3 by addition of dilute hydrochloric acid. The mixture was then extracted with diethyl ether (2×100 ml). The combined organic extracts were dried (MgSO4) and evaporated to give 5-iodobenzo[b]thiophene-2-carboxylic acid (11.7 g) as a solid; NMR (d6 -DMSO): 7.8 (dd, 1H), 7.9 (d, 1H), 8.05 (s, 1H), 8.45 (d, 1H).

Workup

  1. concentrationThe mixture was concentrated to about 150 ml by evaporation
  2. additionby addition of dilute hydrochloric acid
  3. extractionThe mixture was then extracted with diethyl ether (2×100 ml)
  4. dry with materialThe combined organic extracts were dried (MgSO4)
  5. customevaporated

Sources & evidence

ORD record
ord-e83b49efb95f4d37a8d1fba409109821
Source dataset
uspto-grants-2000_07
Patent number
US06087336

Reaction notes

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