1,3,5-Tribromobenzene → Silane, 1,3,5-benzenetriyltris[triethoxy-

HRID 484190Notes

Reaction equation

HRID 484190 reaction equation
[CH2:1]([O:3][Si:4]([O:24][CH2:25][CH3:26])([O:21][CH2:22][CH3:23])[C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([Si:11]([O:18][CH2:19][CH3:20])([O:15][CH2:16][CH3:17])[O:12][CH2:13][CH3:14])[CH:6]=1)[CH3:2].Br[C:28]1[CH:33]=C(Br)C=C(Br)C=1.[I-].[Cs+]>>[CH2:16]([O:15][Si:11]([O:12][CH2:13][CH3:14])([O:18][CH2:19][CH3:20])[C:7]1[CH:8]=[C:9]([Si:4]([O:24][CH2:33][CH3:28])([O:21][CH2:22][CH3:23])[O:3][CH2:1][CH3:2])[CH:10]=[C:5]([Si:4]([O:24][CH2:25][CH3:26])([O:21][CH2:22][CH3:23])[O:3][CH2:1][CH3:2])[CH:6]=1)[CH3:17]

Participants

4

Reactant 3

HCID 122791,3,5-TribromobenzeneHCID 24601Cesium iodideHCID 116037721,3-Bis(triethoxysilyl)benzene

Product 1

HCID 11713854Silane, 1,3,5-benzenetriyltris[triethoxy-

Procedure

The procedure used for the preparation of 1,3-di(triethoxysilyl)benzene was followed using 1,3,5-tribromobenzene (100.0 g, 0.318 mol) in place of 1,3-dibromobenzene. Two distillations gave a clear, colorless oil (0.1 mmHg, 196-198° C., 23.4 g, 13%). Anal. Calcd for C24H48O9Si3 : C, 51.0: H, 8.56. Found: C, 51.2; H, 8.53. IR (Neat, CsI, cm-1) : 2964 s, 2920 s, 2880 s, 2730 w, 1560 m, 1480 w, 1440 m, 1386 s, 1290 m, 1160 s, 1090 vs, 955 s, 825 s, 775 s, 710 m, 670 m, 487 s. 1H NMR (benzene -d6, 22° C., 300 MHz : δ 1.16 (t, J=7.1 Hz, 18 H, OCH2CH 3), 3.87 (q, J=7.1 Hz, 12 H, OCH2CH3, 8.55 (s, 1H, C6H4). 13C{1H} NMR (benzene-d6, 22° C., 75.5 MHz ): δ 18.43 (OCH2CH3), 58.92 (OCH2CH3), 130.83, 143.60 (C6H4).

Workup

  1. customTwo distillations gave a clear, colorless oil (0.1 mmHg, 196-198° C., 23.4 g, 13%)
  2. custom2964 s, 2920 s, 2880 s, 2730 w, 1560 m, 1480 w, 1440 m, 1386 s, 1290 m, 1160 s, 1090 vs, 955 s, 825 s, 775 s, 710 m, 670 m, 487 s
  3. custombenzene -d6, 22° C., 300 MHz

Sources & evidence

ORD record
ord-b6f21b4eb82f4acf8a3c32a05281af82
Source dataset
uspto-grants-1993_07
Patent number
US05229481

Reaction notes

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