4-Fluoroaniline → 2,5-Bis(4-bromophenyl)-1-(4-tert-butylphenyl)pyrrolidine

HRID 1470951Notes

Reaction equation

HRID 1470951 reaction equation
CS(O[CH:6]([C:22]1[CH:27]=[CH:26][C:25]([Br:28])=[CH:24][CH:23]=1)[CH2:7][CH2:8][CH:9](OS(C)(=O)=O)[C:10]1[CH:15]=[CH:14][C:13]([Br:16])=[CH:12][CH:11]=1)(=O)=O.F[C:30]1[CH:36]=[CH:35][C:33]([NH2:34])=[CH:32][CH:31]=1>>[Br:16][C:13]1[CH:14]=[CH:15][C:10]([CH:9]2[CH2:8][CH2:7][CH:6]([C:22]3[CH:27]=[CH:26][C:25]([Br:28])=[CH:24][CH:23]=3)[N:34]2[C:33]2[CH:35]=[CH:36][C:30]([C:10]([CH3:15])([CH3:11])[CH3:9])=[CH:31][CH:32]=2)=[CH:11][CH:12]=1

Participants

3

Reactant 2

HCID 97314-FluoroanilineHCID 582265311,4-Bis(4-bromophenyl)butane-1,4-diyl dimethanesulfonate

Product 1

HCID 582268372,5-Bis(4-bromophenyl)-1-(4-tert-butylphenyl)pyrrolidineYield 81%

Procedure

The product from Example 42B (5.2 g, 9.35 mmol) was subjected to the conditions described in Example 39D, substituting 4-tert-butylaniline (11.91 mL, 74.8 mmol) for 4-fluoroaniline to provide the title product (3.89 g, 81%) as a mixture of isomers.

Sources & evidence

ORD record
ord-36184d768c404fdc8e81c65f7f336084
Source dataset
uspto-grants-2015_04
Patent number
US09006387B2

Reaction notes

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