Imidazole → 4-Chloro-1-iodo-2-[[[tris(1-methylethyl)silyl]oxy]methyl]benzene

HRID 1058257Notes

Reaction equation

HRID 1058257 reaction equation
[CH:1]([Si:4](Cl)([CH:8]([CH3:10])[CH3:9])[CH:5]([CH3:7])[CH3:6])([CH3:3])[CH3:2].[Cl:12][C:13]1[CH:14]=[CH:15][C:16]([I:21])=[C:17]([CH:20]=1)[CH2:18][OH:19].N1C=CN=C1>CN(C=O)C>[Cl:12][C:13]1[CH:14]=[CH:15][C:16]([I:21])=[C:17]([CH:20]=1)[CH2:18][O:19][Si:4]([CH:8]([CH3:10])[CH3:9])([CH:5]([CH3:7])[CH3:6])[CH:1]([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 139400Triisopropylsilyl chlorideHCID 818020(5-Chloro-2-iodophenyl)methanol

Product 1

HCID 186723614-Chloro-1-iodo-2-[[[tris(1-methylethyl)silyl]oxy]methyl]benzeneYield 8,345.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Triisopropylsilylchloride (14.59 mL, 68.16 mmol) was added to a stiffed solution of 5-chloro-2-iodobenzyl alcohol (12.2 g, 45.44 mmol) and imidazole (4.64 g, 68.16 mmol) in DMF (45 mL). After 1 h the mixture was partitioned between hexanes and water. The organic layer was dried (Na2SO4) and evaporated in vacuo to an oil which was purified by flash column chromatography on silica (eluting with 5% methylene chloride/hexanes) to give [(5-chloro-2-iodobenzyl)oxy](triisopropyl)silane as an oil (1611 g): 1H NMR (CDCl3, 400 MHz) δ 1.11 (d, J=6.8 Hz, 18H), 1.20 (septet, J=6.8 Hz, 3H), 4.65 (s, 2H), 6.96 (dd, J=2.6, 8.4 Hz, 1H), 7.56 (d, J=2.8 Hz, 1H), 7.66 (d, J=8.2 Hz, 1H).

Workup

  1. customAfter 1 h the mixture was partitioned between hexanes and water
  2. dry with materialThe organic layer was dried (Na2SO4)
  3. customevaporated in vacuo to an oil which
  4. customwas purified by flash column chromatography on silica (eluting with 5% methylene chloride/hexanes)

Sources & evidence

ORD record
ord-b8867d3165274f9f896c167ab5c0fb3f
Source dataset
uspto-grants-2003_02
Patent number
US06515011B2

Reaction notes

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