Dichlorodiphenylsilane → (1-Naphthyl)diphenylsilanol

HRID 607339

Reaction equation

HRID 607339 reaction equation
[SiH3][OH:2].[C:3]1(Br)[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]=[CH:5][CH:4]=1.C([Li])CCC.Cl[Si:20](Cl)([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>C(OCC)C.O>[C:3]1([Si:20]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[OH:2])[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]=[CH:5][CH:4]=1

Participants

7

Reactant 4

HCID 6627Dichlorodiphenylsilane2×HCID 70011-BromonaphthaleneHCID 142154SilanolHCID 178418339Butyllithium

Product 1

HCID 57572905(1-Naphthyl)diphenylsilanol

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

For preparation of the silanol, 60 mmol 1-naphthyl bromide are metallized with the equimolar amount of n-butyllithium (2 M solution in cyclohexane, 60 mmol) at −20° C. in 400 ml diethyl ether and 60 mmol dichlorodiphenylsilane is then added, in accordance with Example 2.1. After addition of the dichlorodiphenylsilane, the reaction mixture is heated under reflux for 3 h and then hydrolysed by addition of water (100 g). After the organic phase which has been separated off has been washed neutral, the solution is concentrated in vacuo and the crude product is obtained as a white solid. Crude yield: 21.17 g, content: 84% (GC-MS).

Workup

  1. temperaturethe reaction mixture is heated
  2. temperatureunder reflux for 3 h
  3. customAfter the organic phase which has been separated off
  4. washhas been washed neutral
  5. concentrationthe solution is concentrated in vacuo

Sources & evidence

ORD record
ord-11876b3b4d144fda82c77fbf120c9a10
Source dataset
uspto-grants-2011_03
Patent number
US07915457B2

Linked notes

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