Bromine → 5-Bromo-4,4,6,6-tetraethoxy-3,7-dioxa-4,6-disilanonane

HRID 1061479Notes

Reaction equation

HRID 1061479 reaction equation
[CH2:1]([O:3][Si:4]([CH:11]([Li])[Si:12]([O:19][CH2:20][CH3:21])([O:16][CH2:17][CH3:18])[O:13][CH2:14][CH3:15])([O:8][CH2:9][CH3:10])[O:5][CH2:6][CH3:7])[CH3:2].[Br:23]Br>>[CH2:1]([O:3][Si:4]([CH:11]([Br:23])[Si:12]([O:19][CH2:20][CH3:21])([O:16][CH2:17][CH3:18])[O:13][CH2:14][CH3:15])([O:8][CH2:9][CH3:10])[O:5][CH2:6][CH3:7])[CH3:2]

Participants

3

Reactant 2

HCID 24408BromineHCID 178506912HCID 178506912, compound

Product 1

HCID 154365815-Bromo-4,4,6,6-tetraethoxy-3,7-dioxa-4,6-disilanonaneYield 86%

Conditions

Temperature
-78 °C

Procedure

To the lithiated carbanion solution prepared in Example 1 above, a slight excess of bromine (1.5 g, 9.4 mmol) at −78° C. was added. The solution was stirred at −78° C. for 30 minutes and then at RT for 2 hrs. The solvent was pumped off and the product was further extracted with dry pentane. The residue was distilled under vacuum resulting in bis(triethoxysilyl)methylbromide (86% yield): boiling point 144–148° C. at 0.04 mm Hg; 1H NMR (300 MHz, CDCl3) δ 0.55–0.58 (t, 1 H, CHSi), δ 1.18–1.23 (q,18H, CH3) δ 2.89–2.92 (d, 2H, CH2Ph), δ 3.78–3.82 (t, 12H, CH2O), δ 7.17–7.20 (d, 2H, ArH), δ 7.36–7.39 (d, 2H, ArH); 13C NMR (75.48 MHz, CDCl3) δ 10.80 (CHSi), δ 18.46 (CH3), δ 29.47 (CHPh), δ 58.66 (CH2O), δ 130.84, 131.10 (CH aromatic); EI-MS (m/z) 508 (5%, M+), 464 (100%, [M+−44]).

Workup

  1. waitat RT for 2 hrs
  2. extractionthe product was further extracted with dry pentane
  3. distillationThe residue was distilled under vacuum

Sources & evidence

ORD record
ord-9f651d0ba7374ea8b03f4b2bc0b30e16
Source dataset
uspto-grants-2005_11
Patent number
US06960551B2

Reaction notes

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