Triethylamine → HCID 58097282, compound

HRID 1514750Notes

Reaction equation

HRID 1514750 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([I:8])[CH:5]=[CH:4][C:3]=1[OH:9].C(N(CC)CC)C.Cl[Si:18]([CH:25]([CH3:27])[CH3:26])([CH:22]([CH3:24])[CH3:23])[CH:19]([CH3:21])[CH3:20]>C1(C)C=CC=CC=1.CN(C1C=CC=CN=1)C>[Cl:1][C:2]1[CH:7]=[C:6]([I:8])[CH:5]=[CH:4][C:3]=1[O:9][Si:18]([CH:25]([CH3:27])[CH3:26])([CH:22]([CH3:24])[CH3:23])[CH:19]([CH3:21])[CH3:20]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 139400Triisopropylsilyl chlorideHCID 147636412-Chloro-4-iodophenol

Product 1

HCID 58097282HCID 58097282, compoundYield 87.7%

Reagents, catalysts & solvents 2

HCID 218852-DimethylaminopyridineCatalystHCID 1140TolueneSolvent

Procedure

To a solution of 2-chloro-4-iodophenol (351.2 g, 1.38 moles) in toluene (1750 ml) under nitrogen, was added triethylamine (168 g, 1.66 moles), dimethylaminopyridine (8.5 g, 0.069 moles) and chlorotriisopropylsilane (320 g, 1.66 moles), then stirred for 16 hours. After this time the reaction was quenched by the addition of aqueous hydrochloric acid (2M, 1000 ml) and the organic phase washed with water (1000 ml). The solution was dried by azeotropic distillation of toluene, to give the title compound as a clear oil (497 g, 87%).

Workup

  1. customAfter this time the reaction was quenched by the addition of aqueous hydrochloric acid (2M, 1000 ml)
  2. washthe organic phase washed with water (1000 ml)
  3. dry with materialThe solution was dried by azeotropic distillation of toluene

Sources & evidence

ORD record
ord-cc7a81051b214aa2a6f511753f8a6740
Source dataset
uspto-grants-2012_07
Patent number
US08222273B2

Reaction notes

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