1,2-Dibromoethane → HCID 178436186, compound

HRID 1092445Notes

Reaction equation

HRID 1092445 reaction equation
[Mg:1].[CH2:2]([C:4]1[CH:18]=[CH:17][C:7]([CH2:8][C:9]2[CH:14]=[C:13](Br)[CH:12]=[CH:11][C:10]=2[Cl:16])=[CH:6][CH:5]=1)[CH3:3].[Br:19]CCBr>O1CCCC1>[Cl:16][C:10]1[CH:11]=[CH:12][C:13]([Mg:1][Br:19])=[CH:14][C:9]=1[CH2:8][C:7]1[CH:6]=[CH:5][C:4]([CH2:2][CH3:3])=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 78391,2-DibromoethaneHCID 5462224Magnesium3×HCID 115005502-(4-Ethylbenzyl)-4-bromo-1-chlorobenzene2×

Product 1

HCID 178436186HCID 178436186, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Magnesium powder (34.7 g, 1.446 mol) was charged under argon into a three-necked flask followed by the addition of a portion of a solution of 2-(4-ethylbenzyl)-4-bromo-1-chlorobenzene (122.5 g, 0.398 mol) in anhydrous tetrahydrofuran (0.4 L) and 1,2-dibromoethane (2.89 g, 1.34 mL, 0.015 mol). The mixture was heated to reflux and after reaction initiation (exothermic and consuming magnesium), the rest of the solution of 2-(4-ethylbenzyl)-4-bromo-1-chlorobenzene (245.0 g, 0.796 mol) in anhydrous tetrahydrofuran (0.81 L) was added dropwise. The mixture was then allowed to react for another 1 h under gentle reflux until most of the magnesium was consumed.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux
  3. customto react for another 1 h
  4. customwas consumed

Sources & evidence

ORD record
ord-5886e8dcfd0a4f0f84e02e78c22f7ebc
Source dataset
uspto-grants-2012_03
Patent number
US08129434B2

Reaction notes

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