Triethoxychlorosilane → 2-(Triethoxysilyl)thianthrene

HRID 716585Notes

Reaction equation

HRID 716585 reaction equation
[Mg].Cl[Si:3]([O:10][CH2:11][CH3:12])([O:7][CH2:8][CH3:9])[O:4][CH2:5][CH3:6].Br[C:14]1[CH:27]=[CH:26][C:25]2[S:24][C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[S:17][C:16]=2[CH:15]=1>C1COCC1>[CH2:5]([O:4][Si:3]([O:10][CH2:11][CH3:12])([O:7][CH2:8][CH3:9])[C:14]1[CH:27]=[CH:26][C:25]2[S:24][C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[S:17][C:16]=2[CH:15]=1)[CH3:6]

Participants

5

Reactant 3

HCID 78398TriethoxychlorosilaneHCID 5462224MagnesiumHCID 132131222-Bromothianthrene

Product 1

HCID 711166762-(Triethoxysilyl)thianthreneYield 69.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A 3-neck 3 L flask was filled with magnesium turnings (20 g), THF (650 g) and chlorotriethoxysilane (146 g), and heated to reflux. 2-Bromothianthrene from Example 3A was added to the flask in small portions. Grignard started instantly. The reaction was allowed to cool for 1 hour, after which magnesium salts were precipitated with hexanes (500 mL). The solution was filtered, followed by evaporation of volatiles by rotary evaporator. The material was distilled twice at 190 . . . 200° C./<1 mbar, giving colorless 2-(triethoxysilyl)thianthrene (125.9 g, 69.8% overall yield based on thianthrene, purity >99% by GC/MS).

Workup

  1. temperatureheated to reflux
  2. temperatureto cool for 1 hour
  3. customafter which magnesium salts were precipitated with hexanes (500 mL)
  4. filtrationThe solution was filtered
  5. customfollowed by evaporation of volatiles by rotary evaporator
  6. distillationThe material was distilled twice at 190

Sources & evidence

ORD record
ord-aba1dc60b2a644298b01af6eb97ef724
Source dataset
uspto-grants-2015_11
Patent number
US09190616B2

Reaction notes

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