Allyl bromide → Methyl 3-(allyloxy)-4-iodobenzoate

HRID 2181670Notes

Reaction equation

HRID 2181670 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[I:12])[C:5]([O:7][CH3:8])=[O:6].[CH2:13](Br)[CH:14]=[CH2:15].[H-].[Na+]>CN(C=O)C.O>[CH2:15]([O:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[I:12])[C:5]([O:7][CH3:8])=[O:6])[CH:14]=[CH2:13]

Participants

6

Reactant 3

HCID 7841Allyl bromideHCID 24758Sodium hydrideHCID 10378812Methyl 3-hydroxy-4-iodobenzoate

Product 1

HCID 22481791Methyl 3-(allyloxy)-4-iodobenzoateYield 100%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Methyl 3-hydroxy-4-iodobenzoate (2.0 g, 7.2 mmol) is dissolved in DMF (25 ml) in a dry flask under nitrogen. Allyl bromide (0.65 ml, 7.55 mmol) is added drop-wise, followed by the careful addition of 60% NaH (303 mg, 7.55 mmol). The reaction is stirred overnight at RT and then is diluted with H2O (30 ml). The mixture is extracted with EtOAc (3×30 ml), and the combined organics are washed with 50% saturated NaCl (4×25 ml), dried (MgSO4), filtered, and concentrated under high vacuum to an oil that solidified upon standing. The volatiles are removed in vacuo to obtain 2.28 g (100%) of methyl 3-(allyloxy)-4-iodobenzoate as a tan solid. HRMS (FAB) calcd for C11H11IO3+H: 318.9833, found 318.9831 (M+H)+.

Workup

  1. extractionThe mixture is extracted with EtOAc (3×30 ml)
  2. washthe combined organics are washed with 50% saturated NaCl (4×25 ml)
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated under high vacuum to an oil that
  6. customThe volatiles are removed in vacuo

Sources & evidence

ORD record
ord-edb337a036a346a5a921d895a5f030d8
Source dataset
uspto-grants-2005_05
Patent number
US06894042B2

Reaction notes

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