Bromine → Methyl 4-bromo-3-hydroxy-5-methylthiophene-2-carboxylate

HRID 621784Notes

Reaction equation

HRID 621784 reaction equation
[Br:1]Br.[OH:3][C:4]1[CH:8]=[C:7]([CH3:9])[S:6][C:5]=1[C:10]([O:12][CH3:13])=[O:11]>C(O)(=O)C>[Br:1][C:8]1[C:4]([OH:3])=[C:5]([C:10]([O:12][CH3:13])=[O:11])[S:6][C:7]=1[CH3:9]

Participants

4

Reactant 2

HCID 24408BromineHCID 587860Methyl 3-hydroxy-5-methylthiophene-2-carboxylate

Product 1

HCID 54697143Methyl 4-bromo-3-hydroxy-5-methylthiophene-2-carboxylateYield 56.3%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Bromine (4.6 g, 29 mmoles) is added dropwise at room temperature to a stirred solution of methyl 3-hydroxy-5-methyl-2-thiophenecarboxylate (5.0 g, 29 mmoles) in acetic acid (25 mL). After 16 hours the mixture is stirred into ice water (200 mL), and the precipitate is filtered off, rinsed with water, with aqueous sodium thiosulfate, again with water and dried. Recrystallization from methyl t-butyl ether gave the pure product (4.1 g); mp 96°-97° C.

Workup

  1. filtrationthe precipitate is filtered off
  2. washrinsed with water, with aqueous sodium thiosulfate, again with water
  3. customdried
  4. customRecrystallization from methyl t-butyl ether

Sources & evidence

ORD record
ord-8b9cadf2f66d47da880a6a4c28ed3489
Source dataset
uspto-grants-1989_04
Patent number
US04824958

Reaction notes

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