p-Bromobenzenesulfonyl chloride → 1-(4-Bromobenzene-1-sulfonyl)pyrrolidine

HRID 736458Notes

Reaction equation

HRID 736458 reaction equation
[NH:1]1[CH2:5][CH2:4][CH2:3][CH2:2]1.[Br:6][C:7]1[CH:12]=[CH:11][C:10]([S:13](Cl)(=[O:15])=[O:14])=[CH:9][CH:8]=1.[OH-].[Na+]>C(Cl)Cl>[Br:6][C:7]1[CH:12]=[CH:11][C:10]([S:13]([N:1]2[CH2:5][CH2:4][CH2:3][CH2:2]2)(=[O:15])=[O:14])=[CH:9][CH:8]=1

Participants

5

Reactant 3

HCID 7396p-Bromobenzenesulfonyl chlorideHCID 14798Sodium HydroxideHCID 31268Pyrrolidine

Product 1

HCID 7386181-(4-Bromobenzene-1-sulfonyl)pyrrolidineYield 98%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Pyrrolidine (2.5 g, 35.2 mmol) was added to a solution of 4-bromobenzenesulfonyl chloride (4.5 g, 17.6 mmol) in methylene chloride (10 mL) at 0° C. The mixture was stirred for 2 h and an aqueous sodium hydroxide solution (1 M, 5 mL) was added and stirring was continued for another 10 min. The organic phase was separated and diluted with methylene chloride (40 mL), washed with aqueous HCl (1 M, 10 mL), and water (2×10 mL). The organic phase was dried (sodium sulphate) and the solvent was evaporated. The title compound was isolated in 5.0 g (98% yield) as a white solid: 1H NMR (CDCl3, 400 MHz) δ 7.65 (m, 4H), 3.20 (m, 4H), 1.74 (m, 4H); 13C NMR (CDCl3, 100 MHz) δ 135.93, 132.17, 128.84, 127.39, 47.84, 25.13; MS (ES) m/z 290 and 292 (M++1).

Workup

  1. stirringstirring
  2. waitwas continued for another 10 min
  3. customThe organic phase was separated
  4. additiondiluted with methylene chloride (40 mL)
  5. washwashed with aqueous HCl (1 M, 10 mL), and water (2×10 mL)
  6. dry with materialThe organic phase was dried (sodium sulphate)
  7. customthe solvent was evaporated

Sources & evidence

ORD record
ord-b87fe7c7ac3d4e4c99959dd950ec6ed0
Source dataset
uspto-grants-2009_09
Patent number
US07595321B2

Reaction notes

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