Pyrrolidine → 1-((3-Bromo-4-fluorophenyl)sulfonyl)pyrrolidine

HRID 930928Notes

Reaction equation

HRID 930928 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([S:9](Cl)(=[O:11])=[O:10])[CH:5]=[CH:6][C:7]=1[F:8].[NH:13]1[CH2:17][CH2:16][CH2:15][CH2:14]1>ClCCl>[Br:1][C:2]1[CH:3]=[C:4]([S:9]([N:13]2[CH2:17][CH2:16][CH2:15][CH2:14]2)(=[O:11])=[O:10])[CH:5]=[CH:6][C:7]=1[F:8]

Participants

4

Reactant 2

HCID 31268PyrrolidineHCID 218867333-Bromo-4-fluorobenzene-1-sulfonyl chloride

Product 1

HCID 867210711-((3-Bromo-4-fluorophenyl)sulfonyl)pyrrolidineYield 76.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

To a solution of 3-bromo-4-fluorobenzene-1-sulfonyl chloride (1.0 g, 3.66 mmol) in 20 mL dichloromethane at 0° C. was added pyrrolidine (0.635 mL, 7.68 mmol). The mixture was stirred at 0° C. for 30 minutes and then at room temperature overnight. The reaction mixture was diluted with dichloromethane, washed with 1% HCl solution and water, dried over anhydrous magnesium sulfate, filtered, and concentrated to give the title compound (0.86 g, 76% yield)

Workup

  1. customat room temperature
  2. customovernight
  3. washwashed with 1% HCl solution and water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-dcec82a71e1d4276a02de77aeed67fba
Source dataset
uspto-grants-2016_03
Patent number
US09296741B2

Reaction notes

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