Pyridine → HCID 15157157, compound

HRID 1460157Notes

Reaction equation

HRID 1460157 reaction equation
[Br:1]Br.[CH3:3][Si:4]([CH3:21])([O:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1CCO)[C:5]([CH3:10])([CH3:9])[CH:6]([CH3:8])[CH3:7].N1[CH:27]=[CH:26]C=CC=1>C1(C)C=CC=CC=1.CCCCCC>[CH3:21][Si:4]([CH3:3])([O:11][C:12]1[CH:13]=[CH:14][C:15]([CH2:26][CH2:27][Br:1])=[CH:16][CH:17]=1)[C:5]([CH3:9])([CH3:10])[CH:6]([CH3:7])[CH3:8]

Participants

6

Reactant 3

HCID 1049PyridineHCID 24408BromineHCID 53688342HCID 53688342, compound

Product 1

HCID 15157157HCID 15157157, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolvent2×HCID 8058HexaneSolvent

Conditions

Temperature
18 °C

Procedure

To a 0° C. solution of 19.7 g (75 mmol) in 350 mL of toluene was added dropwise over 5 minutes 3.8 mL (74 mmol) of bromine. This was stirred for 50 minutes at which time a solution of 21.0 g (75 mmol) of dimethyl [2-(hydroxy)ethylphenoxy](1,1,2-trimethylpropyl) silane and 6.1 mL (75 mmol) of pyridine in 100 mL of toluene was added dropwise over 10 minutes. The reaction mixture was allowed to warm slowly to 18° C. over 4.3 hours. The mixture was cooled to 0° C. and diluted with 500 mL hexane. The solids were removed by filtration and the filtrate was concentrated in vacuo. The residue was diluted with 500 mL hexane, chilled and passed through a silica gel column. Elution with hexane gave 11.7 g of pure title A bromide.

Workup

  1. additionwas added dropwise over 10 minutes
  2. temperatureThe mixture was cooled to 0° C.
  3. customThe solids were removed by filtration
  4. concentrationthe filtrate was concentrated in vacuo
  5. additionThe residue was diluted with 500 mL hexane
  6. temperaturechilled
  7. washElution with hexane

Sources & evidence

ORD record
ord-ebacfa15de0647b183243b562f75a097
Source dataset
uspto-grants-1991_12
Patent number
US05070099

Reaction notes

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