Bromotrimethylsilane → HCID 13231988, compound

HRID 371301Notes

Reaction equation

HRID 371301 reaction equation
C[Si](Br)(C)C.[OH:6][C:7]1[CH:16]=[CH:15][CH:14]=[C:13]2[C:8]=1[C:9](=[O:40])[CH:10]=[C:11]([C:18]1[C:36]([O:37][CH3:38])=[CH:35][C:34]([CH3:39])=[CH:33][C:19]=1[C:20]([NH:22][CH:23]([P:25](=[O:32])([O:29]CC)[O:26]CC)[CH3:24])=[O:21])[C:12]2=[O:17]>>[OH:6][C:7]1[CH:16]=[CH:15][CH:14]=[C:13]2[C:8]=1[C:9](=[O:40])[CH:10]=[C:11]([C:18]1[C:36]([O:37][CH3:38])=[CH:35][C:34]([CH3:39])=[CH:33][C:19]=1[C:20]([NH:22][CH:23]([P:25](=[O:26])([OH:29])[OH:32])[CH3:24])=[O:21])[C:12]2=[O:17]

Participants

3

Reactant 2

HCID 76113BromotrimethylsilaneHCID 13231987HCID 13231987, compound

Product 1

HCID 13231988HCID 13231988, compoundYield 45%

Procedure

Trimethylsilyl bromide was added to diethyl 1-[2-(5-hydroxy-1,4-naphthoquinon-2-yl)-3-methoxy-5-methylbenzamido]ethylphosphonate (500 mg) as obtained in Example 9 and the mixture was stirred at room temperature for 2 hours. The excess trimethylsilyl bromide was distilled off, water was added to the residue, and the mixture was stirred at room temperature for 30 minutes. The resultant crude crystals were recovered by filtration and recrystallized from methanol. The above procedure gave yellow crystals (200 mg) of 1-[2-(5-hydroxy-1,4-naphthoquinon-2-yl)-3-methoxy-5-methylbenzamido]ethylphosphonic acid.

Workup

  1. customas obtained in Example 9
  2. distillationThe excess trimethylsilyl bromide was distilled off
  3. additionwater was added to the residue
  4. stirringthe mixture was stirred at room temperature for 30 minutes
  5. filtrationThe resultant crude crystals were recovered by filtration
  6. customrecrystallized from methanol

Sources & evidence

ORD record
ord-7d74bbf9ba374b0cac8924a94534a3ff
Source dataset
uspto-grants-1985_07
Patent number
US04530845

Reaction notes

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