1,4-Dibromobenzene → (4-Bromophenyl)(trichloro)silane

HRID 1349924Notes

Reaction equation

HRID 1349924 reaction equation
[Mg].[Br:2][C:3]1[CH:8]=[CH:7][C:6](Br)=[CH:5][CH:4]=1.[Cl:10][Si:11](Cl)([Cl:13])[Cl:12]>C(OCC)C>[Br:2][C:3]1[CH:8]=[CH:7][C:6]([Si:11]([Cl:13])([Cl:12])[Cl:10])=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 78041,4-DibromobenzeneHCID 24816Silicon tetrachlorideHCID 5462224Magnesium

Product 1

HCID 141374(4-Bromophenyl)(trichloro)silane

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

Freshly activated magnesium (8.5 g, 0.35 mol) was slowly added over a period of four hours to a solution of 1,4-dibromobenzene (80 g, 0.34 mol) in 200 mL of diethylether, keeping the temperature below 30° C. The reaction mixture was stirred for 8 hours and then slowly added to a mixture of tetrachlorosilane (100 mL, 0.87 mol) in diethylether (50 mL) within 12 hours. The mixture was stirred for 12 hours, and unreacted tetrachlorosilane and diethylether were removed in vacuum. The remaining liquid was fractionally distilled through a Vigreux column under reduced pressure to provide 4-bromophenyltrichlorosilane as an oil (350 μHg/85° C.-37 g/37%). 1HNMR(400 MHz, CDCl3): δ 7.69 (4H, dd). 13CNMR (100 MHz, CDCl3): δ 134.6, 131.9, 130.4, 128.2. GC-MS: 290 (M+).

Workup

  1. customthe temperature below 30° C
  2. stirringThe mixture was stirred for 12 hours
  3. customunreacted tetrachlorosilane and diethylether were removed in vacuum
  4. distillationThe remaining liquid was fractionally distilled through a Vigreux column under reduced pressure

Sources & evidence

ORD record
ord-d6650885382d4af098a51d0b1c5457b6
Source dataset
uspto-grants-2007_05
Patent number
US07214475B2

Reaction notes

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