Bromotrimethylsilane → 1-Naphthylthiomethanediphosphonic Acid

Reaction equation

[C:1]1([CH:11]([P:20]([O:25]CC)(=[O:24])[O:21]CC)[P:12]([O:17]CC)(=[S:16])[O:13]CC)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.C[Si](Br)(C)C>>[C:1]1([CH:11]([P:20]([OH:24])(=[O:21])[OH:25])[P:12]([OH:13])(=[S:16])[OH:17])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1

Participants

Reactant 2

HCID 76113Bromotrimethylsilane

HCID 86750679Tetraethyl 1-naphthylthiomethanediphosphonate

Product 1

HCID 867506781-Naphthylthiomethanediphosphonic AcidYield 82.1%

Procedure

Following the same method as described in Example 2, 6.70 g (15 mmol) of tetraethyl 1-naphthylthiomethanediphosphonate was treated with trimethylsilyl bromide, and then hydrolyzed to obtain 3.92 g of the title compound as white crystals. The yield was 78%.

Sources & evidence

ORD record: ord-cdd3d03ae0d94a3fa8f2533a66a33143
Source dataset: uspto-grants-1997_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05618804

Reaction notes

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