Sodium Iodide → 4-Iodomethyl benzoic acid tert-butyl ester

HRID 1401889Notes

Reaction equation

HRID 1401889 reaction equation
[I-:1].[Na+].[C:3]([O:7][C:8](=[O:17])[C:9]1[CH:14]=[CH:13][C:12]([CH2:15]Cl)=[CH:11][CH:10]=1)([CH3:6])([CH3:5])[CH3:4]>CC(C)=O>[C:3]([O:7][C:8](=[O:17])[C:9]1[CH:14]=[CH:13][C:12]([CH2:15][I:1])=[CH:11][CH:10]=1)([CH3:6])([CH3:5])[CH3:4]

Participants

4

Reactant 2

HCID 5238Sodium IodideHCID 18959012tert-Butyl 4-(chloromethyl)benzoate

Product 1

HCID 672121184-Iodomethyl benzoic acid tert-butyl esterYield 100%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Sodium iodide (229.2 g) was added to a solution of 4-chloromethyl benzoic acid tert-butyl ester (315.2 g) in acetone (1.5 L). The reaction mixture was heated to reflux for about 2 h and then allowed to cool to room temperature. The precipitate was removed by filtration and the filtrate concentrated under reduced pressure. The residue was partitioned between water (500 mL) and MTBE (1500 mL). The organic phase was washed with saturated sodium bicarbonate and dried over magnesium sulfate. Concentration under reduced pressure afforded 442.2 g (97% yield) dark oil. HNMR: CDCl3, 1.59 ppm (s, 9H), 4.47 (s, 2H), 7.42 (d, 2H), 7.91 (d, 2H)

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for about 2 h
  3. customThe precipitate was removed by filtration
  4. concentrationthe filtrate concentrated under reduced pressure
  5. customThe residue was partitioned between water (500 mL) and MTBE (1500 mL)
  6. washThe organic phase was washed with saturated sodium bicarbonate
  7. dry with materialdried over magnesium sulfate
  8. concentrationConcentration under reduced pressure

Sources & evidence

ORD record
ord-461521255155434faf7c67db3f319f13
Source dataset
uspto-grants-2014_12
Patent number
US08907103B2

Reaction notes

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