Sodium Hydroxide → 3-Bromo-5-(chloromethyl)pyridine

HRID 2277640Notes

Reaction equation

HRID 2277640 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH2:8]O)[CH:5]=[N:6][CH:7]=1.S(Cl)([Cl:12])=O.[OH-].[Na+]>C(Cl)Cl>[Br:1][C:2]1[CH:7]=[N:6][CH:5]=[C:4]([CH2:8][Cl:12])[CH:3]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 24386Thionyl ChlorideHCID 2784733(5-Bromo-3-pyridinyl)methanol

Product 1

HCID 117012593-Bromo-5-(chloromethyl)pyridineYield 93.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (5-bromopyridin-3-yl)methanol (3 g, 16.0 mmol) in DCM (15 mL) cooled to 0° C. was added thionylchloride (7.59 g, 63.8 mmol) dropwise and the reaction mixture was stirred at room temperature overnight. The mixture was poured onto ice/water (20 mL), basified with NaOH conc. (8 mL) and extracted with EtOAc (2×50 mL). Combined organics were dried over Na2SO4, filtered and evaporated to dryness. The residue was purified by silica gel flash chromatography eluting with a 0 to 40% EtOAc-heptane gradient to give the title compound (3.08 g, 93%) as a white solid. MS: 206.0, 207.9 (M+H+).

Workup

  1. additionThe mixture was poured onto ice/water (20 mL)
  2. extractionextracted with EtOAc (2×50 mL)
  3. dry with materialCombined organics were dried over Na2SO4
  4. filtrationfiltered
  5. customevaporated to dryness
  6. customThe residue was purified by silica gel flash chromatography
  7. washeluting with a 0 to 40% EtOAc-heptane gradient

Sources & evidence

ORD record
ord-9cd44b47b29c4194a76e15456a912471
Source dataset
uspto-grants-2015_09
Patent number
US09133158B2

Reaction notes

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