Bromotrimethylsilane → 2-[3-Methoxy-4-hydroxy-1-naphthyl]ethane-1,1-diphosphonic Acid

HRID 53111Notes

Reaction equation

HRID 53111 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:14][CH:15]([P:24]([O:29]CC)(=[O:28])[O:25]CC)[P:16]([O:21]CC)(=[O:20])[O:17]CC)[C:6]2[C:11]([C:12]=1[OH:13])=[CH:10][CH:9]=[CH:8][CH:7]=2.C[Si](Br)(C)C>>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:14][CH:15]([P:16]([OH:21])(=[O:17])[OH:20])[P:24]([OH:29])(=[O:25])[OH:28])[C:6]2[C:11]([C:12]=1[OH:13])=[CH:10][CH:9]=[CH:8][CH:7]=2

Participants

3

Reactant 2

HCID 76113BromotrimethylsilaneHCID 19961540Tetraethyl 2-[3-methoxy-4-hydroxy-1-naphthyl]ethane-1,1-diphosphonate

Product 1

HCID 199615412-[3-Methoxy-4-hydroxy-1-naphthyl]ethane-1,1-diphosphonic AcidYield 67%

Procedure

Following the same method as described in Example 2, 7.12 g (15 mmol) of the tetraethyl 2-[3-methoxy-4-hydroxy-1-naphthyl]ethane-1,1-diphosphonate obtained in Example 11 was treated with trimethylsilyl bromide, and then hydrolysis was effected to obtain 3.64 g of the title compound as pale yellow crystals. The yield was m.p.: 231°-232° C. (dec)

Workup

  1. customhydrolysis

Sources & evidence

ORD record
ord-00ba5370c0644f2eafdeac11cb470d44
Source dataset
uspto-grants-1997_04
Patent number
US05618804

Reaction notes

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