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

HRID 2239452Notes

Reaction equation

HRID 2239452 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([S:8](Cl)(=[O:10])=[O:9])=[CH:4][C:3]=1[F:12].[NH:13]1[CH2:17][CH2:16][CH2:15][CH2:14]1>ClCCl>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:13]2[CH2:17][CH2:16][CH2:15][CH2:14]2)(=[O:10])=[O:9])=[CH:4][C:3]=1[F:12]

Participants

4

Reactant 2

HCID 31268PyrrolidineHCID 27782184-Bromo-3-fluorobenzenesulfonyl chloride

Product 1

HCID 684843891-[(4-Bromo-3-fluorophenyl)sulfonyl]pyrrolidineYield 96%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

According to general procedure C, 4-Bromo-3-fluoro-benzenesulfonyl chloride (0.40 g, 1.46 mmol) and pyrrolidine (0.30 mL, 3.65 mmol) were stirred together with dry dichloromethane (5 mL) for 16 hours. 1-[(4-bromo-3-fluorophenyl)sulfonyl]pyrrolidine (0.43 g, 96%) was provided after purification. HRMS: calcd for C10H11BrFNO2S, 306.96779; found (EI, M+.), 306.968. HPLC purity 100.0% at 210-370 nm, 10.3 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-82b20472e4d94ebdabc56318eccab749
Source dataset
uspto-grants-2010_05
Patent number
US07723332B2

Reaction notes

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