Water → HCID 66618906, compound

HRID 406360Notes

Reaction equation

HRID 406360 reaction equation
S(Cl)([Cl:3])=O.[Br:5][C:6]1[CH:7]=[C:8]([CH:12]([O:15][CH2:16][CH2:17]O)[C:13]#[N:14])[CH:9]=[CH:10][CH:11]=1.O>N1C=CC=CC=1>[Br:5][C:6]1[CH:7]=[C:8]([CH:12]([O:15][CH2:16][CH2:17][Cl:3])[C:13]#[N:14])[CH:9]=[CH:10][CH:11]=1

Participants

5

Reactant 3

HCID 962WaterHCID 24386Thionyl ChlorideHCID 66618856HCID 66618856, compound

Product 1

HCID 66618906HCID 66618906, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
60 °C

Procedure

Thionyl chloride (1.23 mL) was added dropwise to a solution of (3-bromophenyl)-(2-hydroxyethoxy)acetonitrile (3.62 g) in pyridine (12.1 mL) at 50° C., and the mixture was stirred at 60° C. for two hours. Water was added to the reaction solution, followed by extraction with ethyl acetate. The organic layer was washed with water. The organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. Then, the resulting residue was purified by silica gel column chromatography (elution solvent:heptane:ethyl acetate=9:1→8:2) to obtain 3.21 g of the title compound. The property values of the compound are as follows.

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. washThe organic layer was washed with water
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThen, the resulting residue was purified by silica gel column chromatography (elution solvent:heptane:ethyl acetate=9:1→8:2)

Sources & evidence

ORD record
ord-a7d899a60a3944e89f4efef9b23ca41c
Source dataset
uspto-grants-2014_06
Patent number
US08754100B2

Reaction notes

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