Benzyl Bromide → Methyl 3-(benzyloxy)-4-iodobenzoate

HRID 2261798Notes

Reaction equation

HRID 2261798 reaction equation
[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[CH:8][C:7]([I:10])=[C:6]([OH:11])[CH:5]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:19](Br)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>CCCC[N+](CCCC)(CCCC)CCCC.[I-].CC(C)=O>[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[CH:8][C:7]([I:10])=[C:6]([O:11][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:5]=1

Participants

6

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 10378812Methyl 3-hydroxy-4-iodobenzoate

Product 1

HCID 57443321Methyl 3-(benzyloxy)-4-iodobenzoateYield 99.8%

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 180AcetoneSolvent

Conditions

Temperature
50 °C

Procedure

The mixture of 3-hydroxy-4-iodo-benzoic acid methyl ester (1.2 g, 4.3 mmol), potassium carbonate (1.78 g, 13 mmol), acetone (15.0 mL), benzyl bromide (1.5 g, 8.6 mmol), and TBAI (0.05 g) is heated to 50° C. overnight. The solvent is removed under reduced pressure. The residue is partitioned between EtOAc (30 mL) and water (30 mL). The organic phase is washed with brine (20 mL), dried (Na2SO4), filtered, and concentrated under reduced pressure to a residue. The residue is purified by flash chromatography to afford the title compound as white solid (1.58 g, 99%). LC-ES/MS m/e 386.0 (M+18).

Workup

  1. customThe solvent is removed under reduced pressure
  2. customThe residue is partitioned between EtOAc (30 mL) and water (30 mL)
  3. washThe organic phase is washed with brine (20 mL)
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure to a residue
  7. customThe residue is purified by flash chromatography

Sources & evidence

ORD record
ord-ce27fb95ef844d44ae2fc817f47767b2
Source dataset
uspto-grants-2010_12
Patent number
US07846960B2

Reaction notes

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