4-Fluoroaniline → 2,5-Bis(4-chloro-3-nitrophenyl)-1-(4-fluorophenyl)pyrrolidine

HRID 2364786Notes

Reaction equation

CS(O[CH:6]([C:25]1[CH:30]=[CH:29][C:28]([Cl:31])=[C:27]([N+:32]([O-:34])=[O:33])[CH:26]=1)[CH2:7][CH2:8][CH:9](OS(C)(=O)=O)[C:10]1[CH:15]=[CH:14][C:13]([Cl:16])=[C:12]([N+:17]([O-:19])=[O:18])[CH:11]=1)(=O)=O.[F:35][C:36]1[CH:42]=[CH:41][C:39]([NH2:40])=[CH:38][CH:37]=1>O>[Cl:16][C:13]1[CH:14]=[CH:15][C:10]([CH:9]2[CH2:8][CH2:7][CH:6]([C:25]3[CH:30]=[CH:29][C:28]([Cl:31])=[C:27]([N+:32]([O-:34])=[O:33])[CH:26]=3)[N:40]2[C:39]2[CH:41]=[CH:42][C:36]([F:35])=[CH:37][CH:38]=2)=[CH:11][C:12]=1[N+:17]([O-:19])=[O:18]

Participants

Conditions

Temperature: 45 °C

Procedure

The product from Example 28C (2.9 g, 5.2 mmol) and 4-fluoroaniline (5.0 mL, 52.0 mmol) were combined, neat, and heated at 45° C. for 20 h then cooled and poured into water and extracted into dichloromethane. The organics were concentrated the residue was purified by chromatography on silica gel with a 120 g column, eluting with 0-5% ethyl acetate/hexanes to give 0.59 g (24%) of a thick oil.

Workup

temperaturethen cooled
extractionextracted into dichloromethane
concentrationThe organics were concentrated the residue
customwas purified by chromatography on silica gel with a 120 g column
washeluting with 0-5% ethyl acetate/hexanes

Sources & evidence

ORD record: ord-5a9bbd77e6f4406ca7fbbc41b308a53e
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08691938B2

Reaction notes

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