Benzonitrile, 3-(bromomethyl)- → HCID 2819005, compound

HRID 748712Notes

Reaction equation

HRID 748712 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([O-:10])=[O:9])=[CH:4][CH:3]=1.[Na+].Br[CH2:13][C:14]1[CH:15]=[C:16]([CH:19]=[CH:20][CH:21]=1)[C:17]#[N:18]>C(COC)OC>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([CH2:13][C:14]2[CH:15]=[C:16]([CH:19]=[CH:20][CH:21]=2)[C:17]#[N:18])(=[O:10])=[O:9])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 97249Benzonitrile, 3-(bromomethyl)-HCID 23664783Sodium 4-chlorobenzenesulfinate

Product 1

HCID 2819005HCID 2819005, compound

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
70 °C

Procedure

A dimethoxyethane (15 ml) suspension of sodium 4-chlorobenzenesulfinate (270 mg, 1.36 mmol) and 3-bromomethylbenzonitrile (222 mg, 1.13 mmol) was stirred at 70° C. for 3 days. After cooling the reaction mixture to room temperature, the solvent was concentrated under reduced pressure. Ethyl acetate was added to the residue. The mixture was washed successively with water and brine and then, dried over anhydrous sodium sulfate. After filtration, the filtrate was concentrated under reduced pressure. The residue was subjected to flash chromatography on a silica gel column and the fraction obtained from the hexane:ethyl acetate (=3:1) eluate was concentrated under reduced pressure, whereby the title compound (318 mg, 96%) was obtained as a white solid.

Workup

  1. temperatureAfter cooling the reaction mixture to room temperature
  2. concentrationthe solvent was concentrated under reduced pressure
  3. additionEthyl acetate was added to the residue
  4. washThe mixture was washed successively with water and brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationAfter filtration
  7. concentrationthe filtrate was concentrated under reduced pressure
  8. customthe fraction obtained from the hexane
  9. concentrationethyl acetate (=3:1) eluate was concentrated under reduced pressure, whereby the title compound (318 mg, 96%)
  10. customwas obtained as a white solid

Sources & evidence

ORD record
ord-00f1b20316224fb0ae719dc514163366
Source dataset
uspto-grants-2008_07
Patent number
US07399775B2

Reaction notes

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