Hydrochloric Acid → 3-Bromo-5-(chloromethyl)pyridine

HRID 2367671Notes

Reaction equation

HRID 2367671 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH2:8]O)[CH:5]=[N:6][CH:7]=1.[ClH:10]>O1CCOCC1>[ClH:10].[Br:1][C:2]1[CH:7]=[N:6][CH:5]=[C:4]([CH2:8][Cl:10])[CH:3]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 2784733(5-Bromo-3-pyridinyl)methanol

Product 2

HCID 313Hydrochloric AcidHCID 117012593-Bromo-5-(chloromethyl)pyridineYield 66%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

(5-Bromopyridin-3-yl)methanol (XLV) (1.54 g, 8.2 mmol) was treated with 4M HCl in dioxane (10 mL) at 0° C. and then evaporated. The residue was dissolved in SOCl2 (4 mL) and refluxed for 2 hrs. The SOCl2 was removed and the residue was triturated with hexane to produce HCl salt of 3-bromo-5-(chloromethyl)pyridine (XLVI) as a brown solid (1.30 g, 5.4 mmol, 66% yield). The product was used without further purification. ESIMS found for C6H5BrClN m/z 206 (M+H).

Workup

  1. customevaporated
  2. dissolutionThe residue was dissolved in SOCl2 (4 mL)
  3. temperaturerefluxed for 2 hrs
  4. customThe SOCl2 was removed
  5. customthe residue was triturated with hexane

Sources & evidence

ORD record
ord-d2e135fe8a9c498fa80f49a4c311d64d
Source dataset
uspto-grants-2014_04
Patent number
US08697887B2

Reaction notes

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