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

HRID 2277712Notes

Reaction equation

HRID 2277712 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

At 0° C., to a solution of (5-bromopyridin-3-yl)methanol (3 g, 16.0 mmol) in DCM (15 mL) 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), and basified with conc. NaOH solution (8 mL). The mixture was extracted with EtOAc (2×50 mL) and combined organic layers were dried over anhy. 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. extractionThe mixture was extracted with EtOAc (2×50 mL)
  3. customwere dried over anhy
  4. filtrationNa2SO4, filtered
  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-4a93fe99930943b8ac79d8d7added081
Source dataset
uspto-grants-2015_09
Patent number
US09133158B2

Reaction notes

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