Water → 4-Iodo-1-chloro-2-[[4-[[(1,1-dimethylethyl)dimethylsilyl]oxy]phenyl]methyl]benzene

HRID 628756Notes

Reaction equation

HRID 628756 reaction equation
[Cl:1][C:2]1[CH:15]=[CH:14][C:13]([I:16])=[CH:12][C:3]=1[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][CH:6]=1.C(N(CC)CC)C.[Cl-].[C:25]([SiH:29]([CH3:31])[CH3:30])([CH3:28])([CH3:27])[CH3:26].O>C(Cl)Cl.CN(C)C1C=CN=CC=1>[Cl:1][C:2]1[CH:15]=[CH:14][C:13]([I:16])=[CH:12][C:3]=1[CH2:4][C:5]1[CH:6]=[CH:7][C:8]([O:11][Si:29]([C:25]([CH3:28])([CH3:27])[CH3:26])([CH3:31])[CH3:30])=[CH:9][CH:10]=1

Participants

7

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 86698895Phenol, 4-((2-chloro-5-iodophenyl)methyl)-HCID 131722836Tert-butyldimethylsilane chloride

Product 1

HCID 1238887024-Iodo-1-chloro-2-[[4-[[(1,1-dimethylethyl)dimethylsilyl]oxy]phenyl]methyl]benzeneYield 88.2%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

4-(2-chloro-5-iodobenzyl)phenol (8.5 g, 24.7 mmol) and triethylamine (5.0 g, 49.5 mmol) were dissolved in methylene chloride (200 mL). To the resulting mixture were added tert-butyldimethylsilane chloride (5.6 g, 37.1 mmol) and 4-(dimethylamino)pyridine (305 mg, 2.5 mmol) at 0° C. After the completion of addition, the mixture was warmed up to room temperature, and stirred for 18 hr. To the mixture was added water (100 mL). The resulting mixture was separated into an aqueous phase and an organic phase. The aqueous phase was extracted with methylene chloride (100 mL×2). The organic phases were combined, washed with a saturated aqueous sodium chloride solution, dried over anhydrous sodium sulphate, and concentrated under a reduced pressure. The resulting crude product was purified with a silica-gel column chromatography (ethyl acetate:petroleum ether=0-1:100) to produce 10.0 g of a product in a yield of 88%.

Workup

  1. additionAfter the completion of addition
  2. customThe resulting mixture was separated into an aqueous phase
  3. extractionThe aqueous phase was extracted with methylene chloride (100 mL×2)
  4. washwashed with a saturated aqueous sodium chloride solution
  5. dry with materialdried over anhydrous sodium sulphate
  6. concentrationconcentrated under a reduced pressure
  7. customThe resulting crude product was purified with a silica-gel column chromatography (ethyl acetate:petroleum ether=0-1:100)

Sources & evidence

ORD record
ord-9864721d8e6e4c6092ae3013880570c7
Source dataset
uspto-grants-2016_04
Patent number
US09315438B2

Reaction notes

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