Sodium Iodide → Carbonic acid, iodomethyl 4-nitrophenyl ester

HRID 1430724Notes

Reaction equation

HRID 1430724 reaction equation
[C:1](=[O:15])([O:5][C:6]1[CH:11]=[CH:10][C:9]([N+:12]([O-:14])=[O:13])=[CH:8][CH:7]=1)[O:2][CH2:3]Cl.[I-:16].[Na+]>CC(C)=O>[C:1](=[O:15])([O:5][C:6]1[CH:11]=[CH:10][C:9]([N+:12]([O-:14])=[O:13])=[CH:8][CH:7]=1)[O:2][CH2:3][I:16]

Participants

4

Reactant 2

HCID 5238Sodium IodideHCID 2777826Chloromethyl 4-nitrophenyl carbonate

Product 1

HCID 15053075Carbonic acid, iodomethyl 4-nitrophenyl ester

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
45 °C

Procedure

Chloromethyl 4-nitrophenyl carbonate (2.47 g, 10.67 mmol), sodium iodide (1.76 g, 11.73 mmol) were suspended in acetone and heated overnight at 45° C. The yellow suspension was allowed to cool to ambient temperature, concentrated under reduced pressure, diluted with water and aqueous sodium thiosulfate, extracted with dichloromethane, washed with brine, dried over sodium sulfate, and concentrated under reduced pressure to give the title compound as a clear yellow oil. 1H NMR (CDCl3) δ 8.30 (dd, J=7.2, 2.4 Hz, 2H), 7.42 (dd, J=6.8, 2 Hz, 2H), 6.06 (s, 2H).

Workup

  1. temperatureto cool to ambient temperature
  2. concentrationconcentrated under reduced pressure
  3. additiondiluted with water and aqueous sodium thiosulfate
  4. extractionextracted with dichloromethane
  5. washwashed with brine
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-e143ee4fcbc347b3b6a4d4e7fd5537ed
Source dataset
uspto-grants-2015_01
Patent number
US08940912B2

Reaction notes

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