Hydrochloric Acid → Dimethyl 4-chloro-3-hydroxybenzo[b]thiophene-2,5-dicarboxylate

HRID 2395555Notes

Reaction equation

HRID 2395555 reaction equation
[Cl:1][C:2]1[C:11]([C:12]([O:14][CH3:15])=[O:13])=[C:10](Cl)[CH:9]=[CH:8][C:3]=1[C:4]([O:6]C)=O.[C:17]([O:21][CH3:22])(=[O:20])[CH2:18][SH:19].O.[OH-].[Li+].Cl>CN(C)C=O.O>[Cl:1][C:2]1[C:3]2[C:4]([OH:6])=[C:18]([C:17]([O:21][CH3:22])=[O:20])[S:19][C:8]=2[CH:9]=[CH:10][C:11]=1[C:12]([O:14][CH3:15])=[O:13]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 16907Methyl ThioglycolateHCID 168937Lithium hydroxide, monohydrateHCID 18989135Dimethyl 2,4-dichloroisophthaloate

Product 1

HCID 54716697Dimethyl 4-chloro-3-hydroxybenzo[b]thiophene-2,5-dicarboxylateYield 98.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Dimethyl 2,4-dichloroisophthaloate (11.95 g) and methyl thioglycolate (7.23 g) was dissolved in N,N-dimethylformamide, and lithium hydroxide monohydrate (3.81 g) added. The mixture was stirred at ambient temperature for 2 days, diluted with water and brought to pH 1 with hydrochloric acid. The solid was filtered, washed with boiling cyclohexane and dried by azeotropic removal of toluene to give dimethyl 4-chloro-3-hydroxybenzo[b]thiophene-2,5-dicarboxylate (13.44 g) as a beige solid, m.p. 127°-131° C.

Workup

  1. filtrationThe solid was filtered
  2. washwashed with boiling cyclohexane
  3. dry with materialdried by azeotropic removal of toluene

Sources & evidence

ORD record
ord-504109fc8b214f589618298b8722eeca
Source dataset
uspto-grants-1996_02
Patent number
US05489570

Reaction notes

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