Bromotrimethylsilane → 6-Methoxy-2-naphthylthiomethanediphosphonic Acid

HRID 53108Notes

Reaction equation

HRID 53108 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH:9]=[C:8]([CH:13]([P:22]([O:27]CC)(=[O:26])[O:23]CC)[P:14]([O:19]CC)(=[S:18])[O:15]CC)[CH:7]=[CH:6]2.C[Si](Br)(C)C>C(Cl)Cl>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH:9]=[C:8]([CH:13]([P:22]([OH:26])(=[O:23])[OH:27])[P:14]([OH:19])(=[S:18])[OH:15])[CH:7]=[CH:6]2

Participants

4

Reactant 2

HCID 76113BromotrimethylsilaneHCID 86750675Tetraethyl 6-methoxy-2-naphthylthiomethanediphosphonate

Product 1

HCID 867506746-Methoxy-2-naphthylthiomethanediphosphonic AcidYield 80.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Following the same method described as in Example 2, 7.15 g (15 mmol) of tetraethyl 6-methoxy-2-naphthylthiomethanediphosphonate obtained in Example 3 in dry methylene chloride was treated with trimethylsilyl bromide, and then hydrolyzed to obtain 4.21 g of the title compound as white crystals. The yield was 77%.

Sources & evidence

ORD record
ord-25ec6e787a3f4a23aa117cf2e6b6a982
Source dataset
uspto-grants-1997_04
Patent number
US05618804

Reaction notes

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