Benzyl Bromide → 2-(Benzyloxy)-4-ethoxy-5-iodopyridine

HRID 1428535Notes

Reaction equation

HRID 1428535 reaction equation
[CH2:1]([O:3][C:4]1[C:9]([I:10])=[CH:8][N:7]=[C:6]([OH:11])[CH:5]=1)[CH3:2].Br[CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>C1COCC1.C(=O)([O-])[O-].[Ag+2]>[CH2:13]([O:11][C:6]1[CH:5]=[C:4]([O:3][CH2:1][CH3:2])[C:9]([I:10])=[CH:8][N:7]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

5

Reactant 2

HCID 7498Benzyl BromideHCID 178467033HCID 178467033, compound

Product 1

HCID 904176602-(Benzyloxy)-4-ethoxy-5-iodopyridineYield 63.4%

Reagents, catalysts & solvents 2

HCID 178418647HCID 178418647, compoundCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

To a mixture of 4-ethoxy-5-iodopyridin-2-ol (800 mg, 3.02 mmol) in THF (10 mL) was added (bromomethyl)benzene (619 mg, 3.62 mmol) and silver carbonate (1665 mg, 6.04 mmol). The mixture was stirred at 70° C. for 16 h. The reaction residue was filtered and the filtrate was concentrated. The mixture was diluted with H2O and extracted with DCM. The combined organic extract was washed with brine, dried over MgSO4, filtered and concentrated. The resulting 2-(benzyloxy)-4-ethoxy-5-iodopyridine (800 mg, 1.915 mmol, 63.4% yield) was used to next step without further purification: 1H NMR (400 MHz, CDCl3) δ 8.28 (s, 1H), 7.45-7.43 (m, 2H), 7.38-7.36 (m, 3H), 6.22 (s, 1H), 5.33 (s, 2H), 4.12-4.07 (m, 2H), 1.48 (t, J=6.8 Hz, 3H); ES-LCMS m/z 355.9 (M+H).

Workup

  1. filtrationThe reaction residue was filtered
  2. concentrationthe filtrate was concentrated
  3. additionThe mixture was diluted with H2O
  4. extractionextracted with DCM
  5. extractionThe combined organic extract
  6. washwas washed with brine
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-5af745388de0425a8d83eb07ff34c8ab
Source dataset
uspto-grants-2015_01
Patent number
US08937071B2

Reaction notes

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