1,4-Dibromobenzene → 1,4-Didecylbenzene

HRID 2113173Notes

Reaction equation

HRID 2113173 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([Br:8])=[CH:4][CH:3]=1.[CH2:9]([Mg]Br)[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18]>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[Br:1][C:2]1[CH:7]=[C:6]([CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])[C:5]([Br:8])=[CH:4][C:3]=1[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].[CH2:9]([C:2]1[CH:7]=[CH:6][C:5]([CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])=[CH:4][CH:3]=1)[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18]

Participants

5

Reactant 2

HCID 78041,4-Dibromobenzene2×HCID 178418384HCID 178418384, compound

Product 2

HCID 2962691,4-DidecylbenzeneHCID 230725551,4-Dibromo-2,5-didecylbenzene

Reagents, catalysts & solvents 1

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)Catalyst

Procedure

2,5-Dibromo-1,4-didecylbenzene is prepared from 1,4-dibromobenzene in two steps according to literature procedures: decylmagnesium bromide is coupled to 1,4 dibromobenzene using PdCl2(dppf) to yield 1,4-didecylbenzene, which is subsequently treated with bromine to afford 2,5-dibromo-1,4-didecylbenzene.

Sources & evidence

ORD record
ord-c64b8e42f6ef485c8b5aca88784917f4
Source dataset
uspto-grants-2009_04
Patent number
US07524922B2

Reaction notes

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