Phosphorus tribromide → 3-(Bromomethyl)-2-chloropyridine

HRID 593925Notes

Reaction equation

HRID 593925 reaction equation
[Cl:1][C:2]1[C:7]([CH2:8]O)=[CH:6][CH:5]=[CH:4][N:3]=1.[Br:10]P(Br)Br>C(Cl)Cl>[Br:10][CH2:8][C:7]1[C:2]([Cl:1])=[N:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 24614Phosphorus tribromideHCID 2763647(2-Chloropyridin-3-yl)methanol

Product 1

HCID 189310283-(Bromomethyl)-2-chloropyridine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

In a 250 mL round bottom flask was dissolved (2-chloropyridin-3-yl)methanol (6.7 g, 47 mmol) in CH2Cl2 (100 mL). The reaction was cooled to 0° C., to which was slowly added tribromophosphine (4.8 mL, 51 mmol), and allowed to warm to RT overnight. The reaction was quenched by addition of ice, extracted into CH2Cl2, washed 1×NaHCO3, 2×H2O, dried with Mg2SO4, filtered through fritted funnel and filtrate was concentrated. The crude was purified by silica gel chromatography eluting with 15-45% EtOAc/Hex. The product fraction were concentrated down to yield 3-(bromomethyl)-2-chloropyridine as off-white solid. MS m/z=206, 208 [M+1]+. Calc'd for C6H5BrClN: 206.47.

Workup

  1. temperatureto warm to RT overnight
  2. customThe reaction was quenched by addition of ice
  3. extractionextracted into CH2Cl2
  4. washwashed 1×NaHCO3, 2×H2O
  5. dry with materialdried with Mg2SO4
  6. filtrationfiltered through fritted funnel
  7. concentrationfiltrate was concentrated
  8. customThe crude was purified by silica gel chromatography
  9. washeluting with 15-45% EtOAc/Hex
  10. concentrationThe product fraction were concentrated down

Sources & evidence

ORD record
ord-1475b7d10e8345e79d263776500ea740
Source dataset
uspto-grants-2016_01
Patent number
US09242961B2

Reaction notes

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