Thionyl Chloride → HCID 72212581, compound

HRID 623314Notes

Reaction equation

HRID 623314 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[N:5]=[CH:4][C:3]=1[CH2:12]O.O=S(Cl)[Cl:16]>>[Cl:1][C:2]1[C:3]([CH2:12][Cl:16])=[CH:4][N:5]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:7]=1

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 74892530HCID 74892530, compound

Product 1

HCID 72212581HCID 72212581, compoundYield 87%

Procedure

[4-Chloro-6-(trifluoromethyl)pyridin-3-yl]methanol (Int-12) (90 g, 0.426 mol) was added to SOCl2 (700 mL) slowly with ice bath, the mixture was refluxed for 1 hour. The mixture was concentrated and the residue was poured into water (1 L). The mixture was adjusted to pH=7-8 with solid NaHCO3. The mixture was extracted with ethyl acetate (500 mL*3). The combined organic layer was concentrated to yield 4-chloro-5-(chloromethyl)-2-(trifluoromethyl)pyridine (Int-13) (80 g, 87%) as brown syrup which was used for the next step without further purification.

Workup

  1. temperaturethe mixture was refluxed for 1 hour
  2. concentrationThe mixture was concentrated
  3. additionthe residue was poured into water (1 L)
  4. extractionThe mixture was extracted with ethyl acetate (500 mL*3)
  5. concentrationThe combined organic layer was concentrated

Sources & evidence

ORD record
ord-5a9b73d27a68401e8f7b11a019189fc7
Source dataset
uspto-grants-2016_04
Patent number
US09301526B2

Reaction notes

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