Hydrochloric Acid → 1-Bromo-3-(trimethylsilyl)benzene

HRID 1938569Notes

Reaction equation

HRID 1938569 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4](Br)[CH:3]=1.[CH3:9][Si:10](Cl)([CH3:12])[CH3:11].Cl>C(OCC)C>[CH3:9][Si:10]([CH3:12])([CH3:11])[C:4]1[CH:3]=[C:2]([Br:1])[CH:7]=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 6397ChlorotrimethylsilaneHCID 79271,3-Dibromobenzene

Product 1

HCID 41670501-Bromo-3-(trimethylsilyl)benzeneYield 55%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Conditions

Temperature
0 °C

Procedure

A mixture of 1,3-dibromobenzene (25.0 g, 106.4 mmol) and trimethylsilylchloride (11.6 g, 106.4 mmol) in diethyl ether (50 ml) was added dropwise in 11/2 hours on magnesium (2.59 g, 106.4 mmol) in diethyl ether (25 ml). Then the mixture was refluxed for 18 hours, cooled to 0° C., treated with 4N HCl (75 ml). The organic layer was separated, washed with water, brine, dried over MgSO4 and concentrated. 3-Trimethylsilylbromobenzene was obtained by fractional distillation as a colorless oil (13.4 g, 55% yield, b.p.: 55°-62° C. (0.8 mmHg).

Workup

  1. temperatureThen the mixture was refluxed for 18 hours
  2. customThe organic layer was separated
  3. washwashed with water, brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-637b9d6d593f4dea97961058fc68af64
Source dataset
uspto-grants-1997_12
Patent number
US05693668

Reaction notes

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