Sodium Hydroxide → 2-Bromo-5-ethylthiophene-3-carboxylic acid

HRID 1809081Notes

Reaction equation

HRID 1809081 reaction equation
C([O:3][C:4]([C:6]1[CH:10]=[C:9]([CH2:11][CH3:12])[S:8][C:7]=1[Br:13])=[O:5])C.[OH-].[Na+]>O>[Br:13][C:7]1[S:8][C:9]([CH2:11][CH3:12])=[CH:10][C:6]=1[C:4]([OH:5])=[O:3]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 12588560Ethyl2-bromo-5-ethylthiophene-3-carboxylate

Product 1

HCID 595425222-Bromo-5-ethylthiophene-3-carboxylic acidYield 70.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
140 °C

Procedure

2-Bromo-5-ethyl-thiophene-3-carboxylic acid ethyl ester (0.7 g, 2.65 mmol) was dissolved in IMS (4 mL) and aqueous sodium hydroxide (1 M, 6 mL) was added. The reaction was heated to 140° C. using microwave irradiation for 10 minutes. Water (5 mL) was added and the white precipitate formed was isolated by filtration, washed with water and then dried under vacuum to give the title compound (0.44 g). 1H NMR (400 MHz, CHCl3-d): δ 7.1 (s, 1H), 2.7 (q, 2H), 1.25 (t, 3H).

Workup

  1. custommicrowave irradiation for 10 minutes
  2. customthe white precipitate formed
  3. customwas isolated by filtration
  4. washwashed with water
  5. customdried under vacuum

Sources & evidence

ORD record
ord-b8fa958165c549af9c83f0f96aa5bf86
Source dataset
uspto-grants-2013_01
Patent number
US08362008B2

Reaction notes

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