Pyridine → HCID 23157610, compound

HRID 507986Notes

Reaction equation

HRID 507986 reaction equation
[CH2:1]([O:3][CH2:4][CH2:5][O:6][C:7]1[CH:12]=[C:11]([CH3:13])[CH:10]=[C:9]([CH3:14])[C:8]=1[CH3:15])[CH3:2].N1C=CC=CC=1.[Br:22]Br>ClCCl>[Br:22][C:10]1[C:9]([CH3:14])=[C:8]([CH3:15])[C:7]([O:6][CH2:5][CH2:4][O:3][CH2:1][CH3:2])=[CH:12][C:11]=1[CH3:13]

Participants

5

Reactant 3

HCID 1049PyridineHCID 24408BromineHCID 23157476HCID 23157476, compound

Product 1

HCID 23157610HCID 23157610, compoundYield 102.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

To a mixture of 1-(2-ethoxyethoxy)-2,3,5-trimethylbenzene (1.0 g, 4.08 mmol), pyridine (0.097 mL, 1.20 mmol) and dichloromethane (10 mL) was added a solution of bromine (0.66 g, 4.12 mmol) in dichloromethane (1 mL) under stirring at 0° C., and the mixture was stirred at the same temperature for 1 hr. The reaction mixture was washed successively with saturated aqueous sodium hydrogencarbonate solution and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=49/1-hexane/ethyl acetate=4/1) to give the title compound (1.2 g, yield 99%) as a colorless oil.

Workup

  1. stirringthe mixture was stirred at the same temperature for 1 hr
  2. washThe reaction mixture was washed successively with saturated aqueous sodium hydrogencarbonate solution and saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=49/1-hexane/ethyl acetate=4/1)

Sources & evidence

ORD record
ord-dfe7e953381c423e9ff913c9dbfe42d3
Source dataset
uspto-grants-2010_08
Patent number
US07786165B2

Reaction notes

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