Thionyl Chloride → 3-[(6-Bromopyridin-2-yl)(chloro)methyl]benzonitrile

HRID 2099564Notes

Reaction equation

HRID 2099564 reaction equation
[Br:1][C:2]1[N:7]=[C:6]([CH:8](O)[C:9]2[CH:10]=[C:11]([CH:14]=[CH:15][CH:16]=2)[C:12]#[N:13])[CH:5]=[CH:4][CH:3]=1.O=S(Cl)[Cl:20]>C(Cl)Cl>[Br:1][C:2]1[N:7]=[C:6]([CH:8]([Cl:20])[C:9]2[CH:10]=[C:11]([CH:14]=[CH:15][CH:16]=2)[C:12]#[N:13])[CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 860944343-[(6-Bromopyridin-2-yl)(hydroxy)methyl]benzonitrile

Product 1

HCID 860944363-[(6-Bromopyridin-2-yl)(chloro)methyl]benzonitrile

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of 3-[(6-bromopyridin-2-yl)(hydroxy)methyl]benzonitrile (4.88 g, 16.88 mmol) in CH2Cl2 (60 mL) @ 0° C. under N2 was added SOCl2 (2.01 mL, 16.88 mmol). The mixture was warmed to rt and stirred for 48 hr. The mixture was cooled to 0° C. and quenched with saturated aqueous sodium bicarbonate and extracted 3× with CH2Cl2. The combined organics were dried (anhd. Na2SO4), filtered, and concentrated. The residue was purified by silica gel chromatography (25-50% CH2Cl2 in Hexanes) to give 3-[(6-bromopyridin-2-yl)(chloro)methyl]benzonitrile. LRMS m/z (M+H) Calcd.: 307.0, found: 307.0.

Workup

  1. custom@ 0° C. under N2
  2. temperatureThe mixture was cooled to 0° C.
  3. customquenched with saturated aqueous sodium bicarbonate
  4. extractionextracted 3× with CH2Cl2
  5. dry with materialThe combined organics were dried (anhd. Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified by silica gel chromatography (25-50% CH2Cl2 in Hexanes)

Sources & evidence

ORD record
ord-895dd1ff6b8f46de9e8be7d81640ccdd
Source dataset
uspto-grants-2009_08
Patent number
US07569589B2

Reaction notes

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