Water → 2,3-Dihydrobenzofuran-5-sulfonyl Chloride

HRID 1013561Notes

Reaction equation

HRID 1013561 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[CH2:3][CH2:2]1.[S:10]([Cl:13])(Cl)=[O:11].C(Cl)Cl.[OH2:17]>ClCCCl>[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([S:10]([Cl:13])(=[O:11])=[O:17])=[CH:9][C:4]=2[CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 962WaterHCID 6344DichloromethaneHCID 10329DihydrobenzofuranHCID 24386Thionyl Chloride

Product 1

HCID 27761542,3-Dihydrobenzofuran-5-sulfonyl ChlorideYield 100%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Conditions

Temperature
85 °C

Procedure

3.56 g (29.6 mmol) 2,3-dihydrobenzofuran was added to a slurry of 5.44 g (35.5 mmol) sulfur trioxide-N,N-dimethylformamide complex in 12 mL 1,2-dichloroethane under argon. The reaction was heated to 85° C. for 1 hour and then cooled to room temperature. Thionyl chloride (2.6 mL, 35.5 mmol, 1.2 eq) was added dropwise and the reaction was slowly heated over the course of one hour, by which time it had reached 75° C. The mixture was allowed to cool to room temperature and 100 mL of methylene chloride and 100 mL water were added. The organic extract was separated, dried over magnesium sulfate filtered and evaporated to afford 6.56 g (100%) of 2,3-dihydrobenzofuran-5-sulfonyl chloride as a tan oil. (TLC Rf chloroform/hexanes=1/1)

Workup

  1. temperaturecooled to room temperature
  2. temperaturethe reaction was slowly heated over the course of one hour, by which time it
  3. customhad reached 75° C
  4. temperatureto cool to room temperature
  5. extractionThe organic extract
  6. customwas separated
  7. dry with materialdried over magnesium sulfate
  8. filtrationfiltered
  9. customevaporated

Sources & evidence

ORD record
ord-b5a5ddfa943a48ef87cc8d226139e9f9
Source dataset
uspto-grants-2011_07
Patent number
US07981929B2

Reaction notes

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