1,2-Dibromobenzene → (1,2-Phenylene)bis(triethoxysilane)

HRID 484189Notes

Reaction equation

C(O[Si](OCC)(OCC)[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)C.Br[C:28]1[CH:33]=CC=CC=1Br.[I-].[Cs+]>>[CH2:13]([O:12][Si:11]([O:18][CH2:33][CH3:28])([O:15][CH2:16][CH3:17])[C:6]1[CH:5]=[CH:10][CH:9]=[CH:8][C:7]=1[Si:11]([O:12][CH2:13][CH3:14])([O:15][CH2:16][CH3:17])[O:18][CH2:19][CH3:20])[CH3:14]

Participants

Reactant 3

HCID 114141,2-Dibromobenzene

HCID 24601Cesium iodide

HCID 116037721,3-Bis(triethoxysilyl)benzene

Product 1

HCID 21903095(1,2-Phenylene)bis(triethoxysilane)

Procedure

The procedure used for the preparation of 1,3 di(triethoxysilyl) benzene was followed using 1,2 dibromobenzene (100.0 g, 0.424 mg). The product after two distillations was a clear colorless oil (11.9 g, 7%). IR (Neat, CsI, cm-1): 3040 w, 2963 s, 2920 s, 2880 s, 730 w, 1480 w, 1436 m, 1426 w, 1310 w, 1290 w, 1160 s, 1100 vs, 955 s, 780 s, 755 s, 718 m, 700 m, 668 w, 515 m, 484 m. 1H NMR (benzene-d6, 22° C., 300 MHz ): δ 1.21 (t, J=7.2 Hz, 18 H, OCH2CH3), 3.91 (q, J=7.2 Hz, 12H, OCH2CH3), 7.29 (dd, J=5.7 Hz, 2H, C6H4), 8.12 (dd, J=5.7 Hz, 2H, C6H4). 13C{:H} NMR (benzene-d6, 22° C., 75.5 MHz ): δ 18.44 (OCH2CH3), 58.87 (OCH2CH3), 129.25, 137.19, 138.97 (C6H4).

Workup

custom3040 w, 2963 s, 2920 s, 2880 s, 730 w, 1480 w, 1436 m, 1426 w, 1310 w, 1290 w, 1160 s, 1100 vs, 955 s, 780 s, 755 s, 718 m, 700 m, 668 w, 515 m, 484 m

Sources & evidence

ORD record: ord-2cb94f86285c49ea93f5f2f9523b6234
Source dataset: uspto-grants-1993_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05229481

Reaction notes

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