Potassium Nitrate → 4-Fluoro-2-(1-methylcyclohexyl)-5-nitrophenyl methyl carbonate

HRID 404596Notes

Reaction equation

HRID 404596 reaction equation
[C:1](=[O:19])([O:17][CH3:18])[O:2][C:3]1[CH:8]=[CH:7][C:6]([F:9])=[CH:5][C:4]=1[C:10]1([CH3:16])[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]1.[N+:20]([O-])([O-:22])=[O:21].[K+]>S(=O)(=O)(O)O>[C:1](=[O:19])([O:17][CH3:18])[O:2][C:3]1[CH:8]=[C:7]([N+:20]([O-:22])=[O:21])[C:6]([F:9])=[CH:5][C:4]=1[C:10]1([CH3:16])[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]1

Participants

4

Reactant 2

HCID 24434Potassium NitrateHCID 593950614-Fluoro-2-(1-methylcyclohexyl)phenyl methyl carbonate

Product 1

HCID 593950134-Fluoro-2-(1-methylcyclohexyl)-5-nitrophenyl methyl carbonateYield 161.8%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent2×

Procedure

To a solution of 4-fluoro-2-(1-methylcyclohexyl)phenyl methyl carbonate (21.5 g, 81 mmol) in 10 mL of concentrated sulfuric acid was added drop-wise to ice cold mixture of concentrated sulfuric acid (120 mL) and KNO3 (8.2 g, 81 mmol) at 0° C. After addition, the reaction mixture was stirred for 15 min while warming to ambient temperature, poured onto crushed ice, extracted with ethyl acetate (120 mL×3). The organic layer was washed with brine, dried over MgSO4, and evaporated under vacuum. The residue was purified by chromatography on silica gel (hexane:ethyl acetate=100:1) to give 4-fluoro-2-(1-methylcyclohexyl)-5-nitrophenyl methyl carbonate as a yellow oil (40.8 g, 81% yield). 1H NMR (400 MHz, CDCl3) δ 7.90 (d, J=6.8 Hz, 1H), 7.34 (d, J=13.2 Hz, 1H), 3.97 (s, 1H), 2.02-1.96 (m, 2H), 1.73-1.45 (m, 8H), 1.39 (s, 3H).

Workup

  1. additionAfter addition
  2. additionpoured
  3. customonto crushed ice
  4. extractionextracted with ethyl acetate (120 mL×3)
  5. washThe organic layer was washed with brine
  6. dry with materialdried over MgSO4
  7. customevaporated under vacuum
  8. customThe residue was purified by chromatography on silica gel (hexane:ethyl acetate=100:1)

Sources & evidence

ORD record
ord-d996cd3553f84e43a8e9e351375f1f9c
Source dataset
uspto-grants-2014_06
Patent number
US08748612B2

Reaction notes

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