Phosphorus tribromide → 2-(Bromomethyl)-6-methylpyridine

HRID 1625067Notes

Reaction equation

HRID 1625067 reaction equation
[CH3:1][C:2]1[N:7]=[C:6]([CH2:8]O)[CH:5]=[CH:4][CH:3]=1.P(Br)(Br)[Br:11]>C1COCC1>[Br:11][CH2:8][C:6]1[CH:5]=[CH:4][CH:3]=[C:2]([CH3:1])[N:7]=1

Participants

4

Reactant 2

HCID 24614Phosphorus tribromideHCID 707366-Methyl-2-pyridylmethanol

Product 1

HCID 125437332-(Bromomethyl)-6-methylpyridineYield 33.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

(6-methyl-2-pyridinyl)methanol (ALDRICH, 300 mg, 2.436 mmol) were dissolved in 10 mL of anhydrous THF. Phosphorous tribromide (ALDRICH, 0.252 mL, 2.68 mmol) was added. Reaction mixture was stirred at room temperature overnight. Solvent was evaporated and residue was purified by silica column chromatography using hexane:EtOAc as eluents to give a white solid. This solid was partitioned between EtOAc and distilled water (basified with NH3 (32%, aqueous). Organic layer was dried with MgSO4 (anh). Solvent was evaporated to obtain the title compound (152 mg, 0.817 mmol, 33.5% yield). 1H NMR (300 MHz, DMSO-d6) δ ppm: 7.68 (t, 1H), 7.33 (d, 1H), 7.17 (d, 1H), 4.62 (s, 2H), 2.44 (s, 3H). [ES+MS] m/z 186 (M).

Workup

  1. customReaction mixture
  2. customSolvent was evaporated
  3. customresidue was purified by silica column chromatography
  4. customEtOAc as eluents to give a white solid
  5. customThis solid was partitioned between EtOAc
  6. distillationdistilled water (
  7. dry with materialOrganic layer was dried with MgSO4 (anh)
  8. customSolvent was evaporated

Sources & evidence

ORD record
ord-801c481a29a54f398dda1183109e3ce7
Source dataset
uspto-grants-2014_07
Patent number
US08779153B2

Reaction notes

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