7-Chloro-2-ethyl-1H-indene → 2-Ethyl-7-phenyl-1H-indene

HRID 481827Notes

Reaction equation

HRID 481827 reaction equation
[CH2:1]([C:3]1[CH2:4][C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[CH:7][C:6]=2Cl)[CH3:2].[C:13]1([Mg]Br)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>CCOCC>[CH2:1]([C:3]1[CH2:4][C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[CH:7][C:6]=2[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[CH3:2]

Participants

4

Reactant 2

HCID 121494117-Chloro-2-ethyl-1H-indeneHCID 178418255HCID 178418255, compound

Product 1

HCID 184151632-Ethyl-7-phenyl-1H-indeneYield 80%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A 5 L flask was equipped as in Example 3.178 g 2-ethyl-7-chloroindene (1 mol %), 1 L ether and 10.8 g Ni(dpp) (0.02 mol, 2 mol %) added, followed by 355 mL of 3.1M phenylmagnesium bromide in either (1.1 mol, 10% excess). After quenching and work-up by the method described in Example 3, 176 g 2-ethyl-7-phenylindene (0.8 mol) was obtained by vacuum distillation at 140° C. in 80% yield.

Workup

  1. additionadded
  2. customAfter quenching

Sources & evidence

ORD record
ord-62e3eb20837a4ad2b3579cfa86d5f945
Source dataset
uspto-grants-1998_08
Patent number
US05789634

Reaction notes

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