Sulfuric Acid → HCID 59395058, compound

HRID 1465067Notes

Reaction equation

HRID 1465067 reaction equation
[C:1](=[O:14])([O:12][CH3:13])[O:2][C:3]1[CH:8]=[CH:7][C:6]([F:9])=[CH:5][C:4]=1[CH2:10][CH3:11].OS(O)(=O)=O.[N+:20]([O-])([O-:22])=[O:21].[K+]>>[C:1](=[O:14])([O:12][CH3:13])[O:2][C:3]1[CH:8]=[C:7]([N+:20]([O-:22])=[O:21])[C:6]([F:9])=[CH:5][C:4]=1[CH2:10][CH3:11]

Participants

4

Reactant 3

HCID 1118Sulfuric AcidHCID 24434Potassium NitrateHCID 59394984HCID 59394984, compound

Product 1

HCID 59395058HCID 59395058, compoundYield 58%

Conditions

Temperature
0 °C

Procedure

2-Ethyl-4-fluorophenyl methyl carbonate (2.4 g, 12.11 mmol) was added dropwise to H2SO4 (7.2 mL) to generate a yellow homogeneous solution. The solution was then cooled to 0° C. and KNO3 (1.469 g, 14.53 mmol) was added portion-wise maintaining the internal temperature below 5° C. The reaction was stirred for 2 h and then poured on ice water. The aqueous layer was extracted with dichloromethane (3×10 mL), dried over Na2SO4, filtered and concentrated. Purification by silica gel chromatography (10% ethyl acetate/hexane) provided 2-ethyl-4-fluoro-5-nitrophenyl methyl carbonate (1.7 g, 58% yield). 1H NMR (400.0 MHz, DMSO-d6) δ 8.20 (d, J=6.8 Hz, 1H), 7.64 (d, J=12.1 Hz, 2H), 3.88 (s, 3H), 2.62 (q, J=7.5 Hz, 1H), 1.15 (t, J=7.5 Hz, 3H).

Workup

  1. temperaturemaintaining the internal temperature below 5° C
  2. additionpoured on ice water
  3. extractionThe aqueous layer was extracted with dichloromethane (3×10 mL)
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customPurification by silica gel chromatography (10% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-3e309d6475874d8696bbece4df0ba8bf
Source dataset
uspto-grants-2015_04
Patent number
US08999976B2

Reaction notes

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