Chlorotrimethylgermane → HCID 12884908, compound

HRID 466333

Reaction equation

HRID 466333 reaction equation
[Mg].[CH3:2][Ge:3](Cl)([CH3:5])[CH3:4].Br[C:8]1[CH:9]=[C:10]([C:15]2([CH3:20])[O:19][CH2:18][CH2:17][O:16]2)[CH:11]=[C:12](Br)[CH:13]=1>O1CCCC1>[CH3:2][Ge:3]([CH3:5])([CH3:4])[C:8]1[CH:9]=[C:10]([C:15]2([CH3:20])[O:19][CH2:18][CH2:17][O:16]2)[CH:11]=[C:12]([Ge:3]([CH3:5])([CH3:4])[CH3:2])[CH:13]=1.[CH3:2][Ge:3]([CH3:5])([CH3:4])[C:8]1[CH:9]=[C:10]([C:15]2([CH3:20])[O:19][CH2:18][CH2:17][O:16]2)[CH:11]=[CH:12][CH:13]=1

Participants

6

Reactant 3

HCID 73723ChlorotrimethylgermaneHCID 5462224MagnesiumHCID 128849052-(3,5-Dibromophenyl)-2-methyl-1,3-dioxolane

Product 2

HCID 12884908HCID 12884908, compoundYield 65%HCID 146056542-(3-Trimethylgermylphenyl)-2-methyl-1,3-dioxolaneYield 11%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of 108 mg (4.44 mmol) of magnesium and 765 mg (5.00 mmol) of trimethylgermyl chloride was added a solution of 644 mg (2.00 mmol) of 2-(3,5-dibromophenyl)-2-methyl-1,3-dioxolane in 10 ml of tetrahydrofuran at 40° C., stirred in an atmosphere of argon. The mixture was stirred at 70° C. for 4.5 hr. and at room temperature overnight. The reaction mixture was poured into ice-aqueous sodium bicarbonate solution and extracted with methylene chloride. The solvent was removed to give pale brown crystals, which were purified by column chromatography on silica gel [eluent: methylene chloride-n-hexane (1:1)] to give 514 mg (yield 65%) of 2-[3,5-bis(trimethylgermyl)phenyl]-2-methyl-1,3-dioxolane, m.p. 54° C., and 61 mg (yield 11%) of 2-(3-trimethylgermylphenyl)-2-methyl-1,3-dioxolane and 75 mg of the mixture, in which the ratio was 3:2 (by NMR).

Workup

  1. stirringThe mixture was stirred at 70° C. for 4.5 hr
  2. customat room temperature
  3. customovernight
  4. additionThe reaction mixture was poured into ice-aqueous sodium bicarbonate solution
  5. extractionextracted with methylene chloride
  6. customThe solvent was removed
  7. customto give pale brown crystals, which
  8. customwere purified by column chromatography on silica gel [eluent: methylene chloride-n-hexane (1:1)]

Sources & evidence

ORD record
ord-41bd66200ed74803aac1e8f5d1700a2a
Source dataset
uspto-grants-1992_10
Patent number
US05155249

Linked notes

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