1,4-Dioxane → Cyclopentanone, 2-[(2-bromophenyl)methyl]-

Reaction equation

N1([C:6]2[CH2:10][CH2:9][CH2:8][CH:7]=2)CCCC1.[Br:11][C:12]1[CH:19]=[CH:18][CH:17]=[CH:16][C:13]=1[CH2:14]Br.[O:20]1CCOCC1>>[Br:11][C:12]1[CH:19]=[CH:18][CH:17]=[CH:16][C:13]=1[CH2:14][CH:6]1[CH2:7][CH2:8][CH2:9][C:10]1=[O:20]

Participants

Reactant 3

HCID 312751,4-Dioxane

HCID 769652-Bromobenzyl bromide

HCID 81570Pyrrolidine, 1-(1-cyclopenten-1-yl)-

Product 1

HCID 10354892Cyclopentanone, 2-[(2-bromophenyl)methyl]-Yield 45%

Procedure

In a manner similar to that described in Example 82, 1-pyrrolidino-1-cyclopentene (15.1 g, 0.11 mole) in dioxane (100 ml) was treated with 2-bromobenzyl bromide (30.0 g, 0.12 mol) to give the title compound as a clear oil (12.5 g, 45%).

Sources & evidence

ORD record: ord-fc2bcbf414cb447a8d41b3b9d447be96
Source dataset: uspto-grants-1994_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05276053

Reaction notes

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