Chloromethyl[bis(4-fluorophenyl)](2-propoxy)silane → [bis(4-fluorophenyl)]hydroxy(1H-1,2,4-triazol-1-ylmethyl)silane

HRID 1980526Notes

Reaction equation

HRID 1980526 reaction equation
Cl[CH2:2][Si:3]([C:15]1[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=1)([C:8]1[CH:13]=[CH:12][C:11]([F:14])=[CH:10][CH:9]=1)[O:4]C(C)C.[Na].[NH:23]1[CH:27]=[N:26][CH:25]=[N:24]1>CN(C)C=O>[F:14][C:11]1[CH:12]=[CH:13][C:8]([Si:3]([C:15]2[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=2)([OH:4])[CH2:2][N:23]2[CH:27]=[N:26][CH:25]=[N:24]2)=[CH:9][CH:10]=1

Participants

4

Reactant 2

HCID 13392402Chloromethyl[bis(4-fluorophenyl)](2-propoxy)silaneHCID 454898221h-1,2,4-Triazole sodium salt

Product 1

HCID 13474663[bis(4-fluorophenyl)]hydroxy(1H-1,2,4-triazol-1-ylmethyl)silaneYield 30.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 10.0 g (30.6 mmol) of chloromethyl[bis(4-fluorophenyl)](2-propoxy)silane and 3.1 g (30.6 mmol) of 1,2,4-triazole sodium salt in dimethylformamide was stirred at 80°-90° under nitrogen for 2 hours. Workup as in Example 37 gave a waxy solid that was washed with 1:1 ether-hexanes to leave 3.0 g (30%) of the title compound. Recrystallization from chlorobutane gave a purer sample: m.p. 130°-131°; nmr (CDCl3) 4.1 (2H, s), 5.8 (1H, broad s), 7.1 (4H, t), 7.7 (4H, d of d), 7.8 (1H, s), 8.0 (1H, s).

Workup

  1. customWorkup as in Example 37 gave a waxy solid
  2. washthat was washed with 1:1 ether-hexanes

Sources & evidence

ORD record
ord-c3610cb505a449b78ac1a037d92a9b2d
Source dataset
uspto-grants-1985_04
Patent number
US04510136

Reaction notes

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