Water → HCID 131720746, compound

HRID 965268Notes

Reaction equation

HRID 965268 reaction equation
C([Li])CCC.Br[C:7]1[CH:12]=[CH:11][C:10]([Br:13])=[CH:9][CH:8]=1.[Br:14][CH2:15][Si:16](Cl)([CH3:18])[CH3:17].O>C1COCC1>[Br:13][C:10]1[CH:11]=[CH:12][C:7]([CH:15]([Br:14])[SiH:16]([CH3:18])[CH3:17])=[CH:8][CH:9]=1

Participants

6

Reactant 4

HCID 962WaterHCID 78041,4-DibromobenzeneHCID 85476Silane, (bromomethyl)chlorodimethyl-HCID 178418339Butyllithium

Product 1

HCID 131720746HCID 131720746, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of n-butyllithium (2.5M, 53 mL, 0.133 mole) was added dropwise over 30 minutes under argon to a solution of 1,4-dibromobenzene (30.0 g, 0.127 mole) in dry THF (575 mL) at -78° C. After stirring for 1.5 h, bromomethylchlorodimethylsilane (25.0 g, 0.133 mole) was added to the reaction mixture through a canula and the solution was stirred for 1.5 h at -78° C. The reaction was poured into water (325 mL) and extracted with ether. The combined extracts were washed with water and brine, and then dried (Na2SO4) and concentrated in vacuo to an oil. The oil was distilled (Kugelrohr, 110°-125° C., 0.05 mm Hg) to afford the compound as a clear, colorless oil (22.6 g, 58%). 1H NMR (400 MHz, CDCl3) 7.45 (dd, 4H), 2.60 (s, 2H), 0.45 (s, 6H).

Workup

  1. stirringthe solution was stirred for 1.5 h at -78° C
  2. extractionextracted with ether
  3. washThe combined extracts were washed with water and brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated in vacuo to an oil
  6. distillationThe oil was distilled (Kugelrohr, 110°-125° C., 0.05 mm Hg)

Sources & evidence

ORD record
ord-b34810063fcb468abe37b53f8c65f53f
Source dataset
uspto-grants-1998_06
Patent number
US05773512

Reaction notes

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