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Sodium Sulfite → 3-[(2,4,5-trifluorophenyl)sulfonyl]dihydrofuran-2(3H)-one

HRID 548655
Notes
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Reaction equation

HRID 548655 reaction equation
S([O-])([O-])=O.[Na+].[Na+].C(=O)(O)[O-].[Na+].[F:12][C:13]1[CH:18]=[C:17]([F:19])[C:16]([F:20])=[CH:15][C:14]=1[S:21](Cl)(=[O:23])=[O:22].Br[CH:26]1[CH2:30][CH2:29][O:28][C:27]1=[O:31]>O>[F:12][C:13]1[CH:18]=[C:17]([F:19])[C:16]([F:20])=[CH:15][C:14]=1[S:21]([CH:26]1[CH2:30][CH2:29][O:28][C:27]1=[O:31])(=[O:23])=[O:22]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 24437Sodium SulfiteHCID 954632(3H)-Furanone, 3-bromodihydro-HCID 516892Sodium BicarbonateHCID 27769792,4,5-Trifluorobenzenesulfonyl chloride

Product 1

HCID 576631723-[(2,4,5-trifluorophenyl)sulfonyl]dihydrofuran-2(3H)-oneYield 17.7%

Reagents, catalysts & solvents 1

HCID 962
Water
Solvent

Conditions

Temperature
150 °C

Procedure

A solution of sodium sulfite (153 mg, 1.21 mmol) and sodium bicarbonate (306 mg, 3.63 mmol) in water (3 mL) was treated with 2,4,5-trifluorobenzenesulfonyl chloride (280 mg, 1.21 mmol) and heated in a microwave reactor at 150° C. for 400 seconds. The resulting mixture was treated with 3-bromodihydrofuran-2(3H)-one (299 mg, 1.82 mmol) and then heated in a microwave reactor at 150° C. for 500 seconds. The mixture was cooled to 10° C. and the resulting solid filtered off and dried in vacuo to give the title compound (60 mg).

Workup

  1. temperatureheated in a microwave reactor at 150° C. for 500 seconds
  2. temperatureThe mixture was cooled to 10° C.
  3. filtrationthe resulting solid filtered off
  4. customdried in vacuo

Sources & evidence

ORD record
ord-62ad255cfeca4823b32d841fc3874fea
Source dataset
uspto-grants-2011_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07943607B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes