Hydrochloric Acid → 5-Bromo-3-phenylbenzo[b]thiophene-2-carboxylic acid

HRID 328991Notes

Reaction equation

HRID 328991 reaction equation
[Br:1][C:2]1[CH:20]=[CH:19][C:5]2[S:6][C:7]([C:15]([O:17]C)=[O:16])=[C:8]([C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=3)[C:4]=2[CH:3]=1.[OH-].[Na+].Cl>CO>[Br:1][C:2]1[CH:20]=[CH:19][C:5]2[S:6][C:7]([C:15]([OH:17])=[O:16])=[C:8]([C:9]3[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=3)[C:4]=2[CH:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 22763497Methyl 5-bromo-3-phenylbenzo[b]thiophene-2-carboxylate

Product 1

HCID 227634685-Bromo-3-phenylbenzo[b]thiophene-2-carboxylic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Heat 3 g. of methyl 5-bromo-3-phenyl-benzo[b]-thiophene-2-carboxylate in a mixture of 50 ml. of methanol and 30 ml of 10% sodium hydroxide under reflux for one hour. Add concentrated hydrochloric acid to yield the title compound as a precipitate. Recrystallize it from benzene; m.p. 265°-266°.

Workup

  1. temperatureHeat 3 g

Sources & evidence

ORD record
ord-f51ae64d2802413391de96272bdbbaee
Source dataset
uspto-grants-1977_04
Patent number
US04018893

Reaction notes

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