Nitric Acid → 2-Chloro-4-fluoro-5-nitrophenyl methyl carbonate

HRID 2042053Notes

Reaction equation

HRID 2042053 reaction equation
[C:1](=[O:13])([O:11][CH3:12])[O:2][C:3]1[CH:8]=[CH:7][C:6]([F:9])=[CH:5][C:4]=1[Cl:10].[N+:14]([O-])([OH:16])=[O:15]>OS(O)(=O)=O>[C:1](=[O:13])([O:11][CH3:12])[O:2][C:3]1[CH:8]=[C:7]([N+:14]([O-:16])=[O:15])[C:6]([F:9])=[CH:5][C:4]=1[Cl:10]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 104884382-Chloro-4-fluoro-methoxycarbonyloxybenzene

Product 1

HCID 37866902-Chloro-4-fluoro-5-nitrophenyl methyl carbonateYield 90%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent2×

Procedure

To a suspension of 2-chloro-4-fluorophenyl methyl carbonate (110 g, 0.54 mol) in conc. H2SO4 (50 mL) was slowly added a mixture comprised of conc. H2SO4 (40 mL) and fuming HNO3 (40.8 mL, 0.89 mol). The resultant mixture was stirred for 30 min at 0° C. The reaction mixture was poured into ice water and the precipitated solid was collected by filtration and washed with water to give 2-chloro-4-fluoro-5-nitrophenyl methyl carbonate (120 g, 90% yield). 1H NMR (400 MHz, DMSO-d6): δ 8.45 (d, J=7.2 Hz, 1H), 8.12 (d, J=10.8 Hz, 1H), 3.89 (s, 3H); MS (ESI) m/z: 250.1 (M+H+).

Workup

  1. additionwas slowly added a mixture
  2. filtrationthe precipitated solid was collected by filtration
  3. washwashed with water

Sources & evidence

ORD record
ord-e4f71804bd5b424ba0b7f1d6bf022b47
Source dataset
uspto-grants-2013_11
Patent number
US08586565B2

Reaction notes

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