Sodium Iodide → HCID 46919443, compound

HRID 77351

Reaction equation

HRID 77351 reaction equation
[F:1][C:2]1[CH:12]=[CH:11][C:5]([C:6]([O:8][CH2:9]Cl)=[O:7])=[CH:4][CH:3]=1.[Na+].[I-:14]>CC(C)=O>[F:1][C:2]1[CH:12]=[CH:11][C:5]([C:6]([O:8][CH2:9][I:14])=[O:7])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 5238Sodium IodideHCID 11401232Chloromethyl 4-fluorobenzoate

Product 1

HCID 46919443HCID 46919443, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of chloromethyl 4-fluorobenzoate (3.0g, 15.9 mmol) in 50 mL of dry acetone, NaI (4.8 g, 31.8 mmol) was added and the mixture was stirred overnight. The solvent was removed and Et2O (150 mL) was added to the solid residues and the mixture was stirred for 10 min. After filtration the filtrate was washed with 5% NaHSO3 (aq) (2×25 mL) followed by brine. The organic solution was concentrated by rotary evaporation and purified by silica gel chromatography to give a light yellow oil. Yield 3.7 g (85%). 1H NMR (300 MHz, CDCl3): δ 6.16 (s, 2H), 7.17 (m, 2H), 8.08 (m, 2H).

Workup

  1. customThe solvent was removed
  2. additionEt2O (150 mL) was added to the solid residues
  3. stirringthe mixture was stirred for 10 min
  4. filtrationAfter filtration the filtrate
  5. washwas washed with 5% NaHSO3 (aq) (2×25 mL)
  6. concentrationThe organic solution was concentrated by rotary evaporation
  7. custompurified by silica gel chromatography
  8. customto give a light yellow oil

Sources & evidence

ORD record
ord-3a7da02939a042cb873473416ffb7bfe
Source dataset
uspto-grants-2014_09
Patent number
US08841257B2

Linked notes

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