Sodium Iodide → Carbonic acid, iodomethyl 4-nitrophenyl ester

HRID 2415513Notes

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

Conditions

Temperature: 40 °C

Procedure

Chloromethyl p-nitrophenyl carbonate (52) (100 g, 0.43 moles), sodium iodide (228 g, 1.30 moles) and 50 g of dried molecular sieves (4 Å) were added to 2 L of acetone under nitrogen with mechanical stirring. The resulting mixture was stirred at 40° C. for 5 hours (monitored by 1H NMR). Upon completion, the solid materials were removed by filtration and the solvent was removed under reduced pressure. The residue was redissolved in dichloromethane (1 L) and washed twice with saturated aqueous sodium carbonate (300 mL) followed by water (300 mL). The organic layer was separated and dried over anhydrous sodium sulfate. Removal of solvent gave 123.6 g (89%) of the title compound (53) as a solid upon standing. The compound was found to be unstable to LC-MS. 1H NMR (CDCl3, 400 MHz): 6.06 (s, 2H), 7.42 (d, J=9 Hz, 2H), 8.30 (d, J=9 Hz, 2H). 13C NMR (CDCl3, 100 MHz): 155.1, 151.0, 146.0, 125.8, 125.7, 121.9, 33.5.

Workup

customUpon completion, the solid materials were removed by filtration
customthe solvent was removed under reduced pressure
dissolutionThe residue was redissolved in dichloromethane (1 L)
washwashed twice with saturated aqueous sodium carbonate (300 mL)
customThe organic layer was separated
dry with materialdried over anhydrous sodium sulfate
customRemoval of solvent

Sources & evidence

ORD record: ord-8eb395da2ba94759a547723b0adb4107
Source dataset: uspto-grants-2004_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06818787B2

Reaction notes

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