1,4-Dichlorobenzene → 2-Bromo-1,4-dichlorobenzene

HRID 68021

Reaction equation

HRID 68021 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[Br:5]C1C=CC=CC=1.[CH:12]1[C:17]([Cl:18])=[CH:16][CH:15]=[C:14]([Cl:19])[CH:13]=1.[Br:20][C:21]1[CH:26]=[CH:25][C:24]([Cl:27])=[C:23]([Cl:28])[C:22]=1[Br:29]>[Fe]>[Br:29][C:22]1[CH:21]=[CH:26][C:25]([Cl:18])=[CH:24][C:23]=1[Cl:28].[Br:5][C:15]1[CH:16]=[C:17]([Cl:18])[CH:12]=[CH:13][C:14]=1[Cl:19].[Br:20][C:21]1[CH:26]=[CH:25][C:24]([Cl:27])=[C:23]([Cl:28])[CH:22]=1

Participants

8

Reactant 4

HCID 46851,4-DichlorobenzeneHCID 7961BromobenzeneHCID 6451240Aluminum(III) ChlorideHCID 140296631,2-dibromo-3,4-dichlorobenzene

Product 3

HCID 150332-Bromo-1,4-dichlorobenzeneHCID 290134-Bromo-1,2-dichlorobenzeneHCID 709471-Bromo-2,4-dichlorobenzene

Reagents, catalysts & solvents 1

HCID 23925IronCatalyst

Procedure

The o-, m- or p-dichlorobenzenes or mixture thereof which is used as intermediates for syntheses of various organic compounds is brominated at 0° to 100° C. in the presence of aluminum chloride, ferric chloride or iron powder. The bromobenzene is chlorinated in the same condition. The dichlorobenzene is reacted with the dibromodichlorobenzene in the presence of an aluminum halide for 1 to 5 hours. In these methods, 1-bromo-2,4-dichlorobenzene, 1-bromo-2,5-dichlorobenzene, and 1-bromo-3,4-dichlorobenzene etc. can be obtained in high yield.

Sources & evidence

ORD record
ord-12b808519d014a45884e6fff12f972d8
Source dataset
uspto-grants-1982_08
Patent number
US04347390

Linked notes

Loading…