Carbon Dioxide → 4-Bromo-3-thenoic acid

HRID 1939026Notes

Reaction equation

HRID 1939026 reaction equation
Br[C:2]1[C:6]([Br:7])=[CH:5][S:4][CH:3]=1.[Li]C(C)(C)C.[C:13](=[O:15])=[O:14]>CCOCC.CCCCC>[Br:7][C:6]1[C:2]([C:13]([OH:15])=[O:14])=[CH:3][S:4][CH:5]=1

Participants

6

Reactant 3

HCID 280Carbon DioxideHCID 184523,4-DibromothiopheneHCID 178418306HCID 178418306, compound

Product 1

HCID 855464-Bromo-3-thenoic acidYield 70.3%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolvent2×HCID 8003PentaneSolvent

Conditions

Temperature
-78 °C

Procedure

To a solution of 3,4-dibromothiophene (15 g, 62 mmol) in 80 mL ether under a positive nitrogen atmosphere was added dropwise 75 mL 1.7M t-BuLi in pentane at below -73° C. and the resulting reaction solution was stirred at -78° C. for 0.5 h. After that, the ether solution was poured into dry ice and extracted with water. The aq solution was washed with ether and then acidified with concentrated HCl. The solid was filtered and air-dried to give 9 g of 4-bromo-3-thiophenecarboxylic acid, yield 70.3%.

Workup

  1. customthe resulting reaction solution
  2. extractionextracted with water
  3. washThe aq solution was washed with ether
  4. filtrationThe solid was filtered
  5. customair-dried

Sources & evidence

ORD record
ord-2ee2496b07f746bfb29aef2ee56b4e86
Source dataset
uspto-grants-1997_12
Patent number
US05693667

Reaction notes

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