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

HRID 2239399Notes

Reaction equation

HRID 2239399 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([S:8](Cl)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[NH:12]1[CH2:16][CH2:15][CH2:14][CH2:13]1>ClCCl>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:12]2[CH2:16][CH2:15][CH2:14][CH2:13]2)(=[O:10])=[O:9])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 7396p-Bromobenzenesulfonyl chlorideHCID 31268Pyrrolidine

Product 1

HCID 7386181-(4-Bromobenzene-1-sulfonyl)pyrrolidineYield 26.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

According to general procedure C, 4-Bromobenzene sulfonyl chloride (0.40 g, 1.56 mmol) and pyrrolidine (0.32 mL, 3.90 mmol) were stirred together in dry dichloromethane (5 mL) for 16 hours. 1-[(4-bromophenyl)sulfonyl]pyrrolidine (0.12 g) was provided after purification. HRMS: calcd for C10H12BrNO2S+H+, 289.98449; found (ESI, [M+H]+), 289.9847. HPLC purity 99.1% at 210-370 nm, 8.9 min.; the Xterra® RP18 column, 3.5μ, 150×4.6 mm column, 1.2 mL/min., 85/15-5/95 (ammonium formate buffer pH=3.5/ACN+MeOH) for 10 min., hold 4 min.

Sources & evidence

ORD record
ord-6537bf04ac0f45608f535cba1178e78e
Source dataset
uspto-grants-2010_05
Patent number
US07723332B2

Reaction notes

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