Sodium Carbonate → 5-Bromo-2-thiopheneacetic acid

HRID 410027Notes

Reaction equation

HRID 410027 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][C:7]([OH:9])=[O:8].[Br:10]Br.C(=O)([O-])[O-].[Na+].[Na+]>CC(O)=O.O>[Br:10][C:5]1[S:1][C:2]([CH2:6][C:7]([OH:9])=[O:8])=[CH:3][CH:4]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 159702-Thiopheneacetic acidHCID 24408Bromine

Product 1

HCID 33350865-Bromo-2-thiopheneacetic acid

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

To a solution of 2-(thiophen-2-yl)acetic acid (2 g, 14 m mol) in HOAc (10 ml) was added dropwise bromine (2.25 g, 14 mmol) at 10-20° C. for 30 min. The mixture was allowed to warm to room temperature for 3 hours. Then it was diluted with water (100 ml), neutralized to pH=5 with anhydrous sodium carbonate and extracted with EtOAc (100 ml×3). Dried over Na2SO4, filtered and concentrated to afford crude product as brown oil. MS (ESI): m/z 220.9 [M+1]+.

Workup

  1. extractionextracted with EtOAc (100 ml×3)
  2. dry with materialDried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customto afford crude product as brown oil

Sources & evidence

ORD record
ord-f0442be2fb0646eaa38a302df0d1b125
Source dataset
uspto-grants-2014_06
Patent number
US08759548B2

Reaction notes

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