Sodium Thiosulfate → HCID 66584943, compound

HRID 589881Notes

Reaction equation

HRID 589881 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:8]2[C:9]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:10][NH:11][CH:12]=2)[CH:5]=[CH:6][CH:7]=1.[Br:18]N1C(=O)CCC1=O.S([O-])([O-])(=O)=S.[Na+].[Na+]>O1CCCC1>[Br:18][C:12]1[NH:11][CH:10]=[C:9]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[C:8]=1[C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([F:1])[CH:3]=1

Participants

5

Reactant 3

HCID 24477Sodium ThiosulfateHCID 67184N-bromobutanimideHCID 66584760HCID 66584760, compound

Product 1

HCID 66584943HCID 66584943, compoundYield 33.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 38.3 g (164 mmol) of ethyl 4-(3-fluorophenyl)-1H-pyrrole-3-carboxylate in 380 ml of tetrahydrofuran are added, over 30 minutes, 32.1 g (181 mmol) of N-bromosuccinimide (CAS 128-08-5), and the mixture is then stirred for 3 hours at reflux. After cooling, 200 ml of aqueous 5% sodium thiosulfate solution are added and the reaction product is extracted with ethyl acetate. The organic phase is dried over sodium sulfate and the solvent is evaporated off under reduced pressure, to give 17.1 g of ethyl 5-bromo-4-(3-fluorophenyl)-1H-pyrrole-3-carboxylate in the form of a white powder after recrystallizing from diisopropyl ether, filtering off and drying.

Workup

  1. temperatureat reflux
  2. temperatureAfter cooling
  3. extractionthe reaction product is extracted with ethyl acetate
  4. dry with materialThe organic phase is dried over sodium sulfate
  5. customthe solvent is evaporated off under reduced pressure

Sources & evidence

ORD record
ord-b0903ec3b8244e43a709dea1b835d2eb
Source dataset
uspto-grants-2016_01
Patent number
US09233965B2

Reaction notes

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