Nitric Acid → HCID 69386549, compound

HRID 860967Notes

Reaction equation

HRID 860967 reaction equation
[CH3:1][O:2][C:3](=[O:25])[CH2:4][C:5]1[CH:10]=[C:9]([Br:11])[C:8]([O:12][C:13]2[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[C:15]([CH:21]([CH3:23])[CH3:22])[CH:14]=2)=[C:7]([Br:24])[CH:6]=1.CCCCCCC.C(OCC)(=O)C.[N+:39]([O-])([OH:41])=[O:40]>C1C=CC=CC=1>[CH3:1][O:2][C:3](=[O:25])[CH2:4][C:5]1[CH:10]=[C:9]([Br:11])[C:8]([O:12][C:13]2[CH:14]=[C:15]([CH:21]([CH3:23])[CH3:22])[C:16]([O:19][CH3:20])=[C:17]([N+:39]([O-:41])=[O:40])[CH:18]=2)=[C:7]([Br:24])[CH:6]=1

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 11123548HCID 11123548, compoundHCID 21899848Ethylacetate heptane

Product 1

HCID 69386549HCID 69386549, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To a solution of methyl[3,5-dibromo-4-(3-isopropyl-4-methoxyphenoxy)phenyl]acetate (1.0 g, 2.12 mmol) in benzene (150 mL), nitric acid (0.81 mL, 65%) was added drop-wise. The mixture was further stirred for 1 hour at room temperature. The reaction was monitored by TLC (65:35 n-heptane/ethyl acetate) and the reaction mixture was quenched with a saturated aqueous solution of sodium hydrogen carbonate. The resulting organic and aqueous phases were separated and the aqueous phase was extracted with ethyl acetate. The combined organic phase was washed with water, brine, and the organic phase was dried over magnesium sulfate, and concentrated. The crude product was crystallized from methanol to give 1.1 g, (99%) of methyl[3,5-dibromo-4-(5-isopropyl-4-methoxy-3-nitrophenoxy)phenyl]acetate.

Workup

  1. customthe reaction mixture was quenched with a saturated aqueous solution of sodium hydrogen carbonate
  2. customThe resulting organic and aqueous phases were separated
  3. extractionthe aqueous phase was extracted with ethyl acetate
  4. washThe combined organic phase was washed with water, brine
  5. dry with materialthe organic phase was dried over magnesium sulfate
  6. concentrationconcentrated
  7. customThe crude product was crystallized from methanol

Sources & evidence

ORD record
ord-75807a86bac74693ba20545b894147b3
Source dataset
uspto-grants-2006_12
Patent number
US07153997B2

Reaction notes

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