Hydrochloric Acid → 4-Bromo-3-methylthiophenecarboxylic acid

HRID 2269670Notes

Reaction equation

HRID 2269670 reaction equation
[Br:1][C:2]1[C:3]([CH3:12])=[C:4]([C:7]([O:9]CC)=[O:8])[S:5][CH:6]=1.[OH-].[Na+].Cl.O>C1COCC1.CO.O>[Br:1][C:2]1[C:3]([CH3:12])=[C:4]([C:7]([OH:9])=[O:8])[S:5][CH:6]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 18347936Ethyl 4-bromo-3-methylthiophene-2-carboxylate

Product 1

HCID 27570734-Bromo-3-methylthiophenecarboxylic acidYield 86%

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

To a solution of ethyl 4-bromo-3-methyl-2-thiophenecarboxylate (5.0 g, 0.0201 mol) in THF/MeOH/H2O (4:1:1, v/v/v, 50 mL) was added NaOH (1.00 g, 0.0251 mol) and the resulting mixture was stirred at ambient temperature overnight. The mixture was acidified by adding 6 N HCl (100 mL) and water (100 mL). The resulting fine white precipitate was filtered off, washed with water and dried to give 3.80 g (86%) of 4-bromo-3-methyl-2-thiophenecarboxylic acid as a fine white solid, mp 188-189° C.

Workup

  1. filtrationThe resulting fine white precipitate was filtered off
  2. washwashed with water
  3. customdried

Sources & evidence

ORD record
ord-8af8db155aa64d369dd1162e433b7f8c
Source dataset
uspto-grants-2001_12
Patent number
US06329528B1

Reaction notes

Loading…