Water → (3-Bromophenyl)trimethylsilane

HRID 1522726Notes

Reaction equation

HRID 1522726 reaction equation
C([Li])CCC.[Br:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9](Br)[CH:8]=1.[CH3:14][Si:15](Cl)([CH3:17])[CH3:16].O>CCOCC>[Br:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([Si:15]([CH3:17])([CH3:16])[CH3:14])[CH:8]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6397ChlorotrimethylsilaneHCID 79271,3-DibromobenzeneHCID 178418339Butyllithium

Product 1

HCID 4167050(3-Bromophenyl)trimethylsilaneYield 100.2%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

n-Butyllithium (38 cm3, 1.6 M in hexanes) was added dropwise to a solution of 1,3-dibromobenzene (5.1 cm3, 42 mmol) in ether (200 cm3) cooled in a dry ice/acetone bath, and the reaction was stirred for 1 hour. A solution of trimethylsilylchloride (21 cm3, 170 mmol) in ether (20 cm3) was added, and the reaction was stirred for 20 hours, gradually warming to room temperature. Water (200 cm3) was added, and the layers were separated. The aqueous layer was extracted with ether (3×50 cm3). The combined organic extracts were washed with brine (300 cm3) and dried over magnesium sulfate, and the solvent was removed to leave a colourless oil. The crude product was passed through a plug of silica using 30-40 light petroleum as the eluent, to give (21) as a colourless oil (9.65 g, 99%).

Workup

  1. temperaturecooled in a dry ice/acetone bath
  2. stirringthe reaction was stirred for 20 hours
  3. customthe layers were separated
  4. extractionThe aqueous layer was extracted with ether (3×50 cm3)
  5. washThe combined organic extracts were washed with brine (300 cm3)
  6. dry with materialdried over magnesium sulfate
  7. customthe solvent was removed
  8. customto leave a colourless oil

Sources & evidence

ORD record
ord-ebb91ec2c18b4bc2b440fc0e9646ca32
Source dataset
uspto-grants-2015_07
Patent number
US09078330B2

Reaction notes

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