Hydrochloric Acid → HCID 53859083, compound

HRID 1417532Notes

Reaction equation

HRID 1417532 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:10]2[CH:14](OC)[O:13][N:12]=[C:11]2[CH3:17])[CH:5]=[CH:6][C:7]=1[O:8][CH3:9].Cl>C(O)C>[Br:1][C:2]1[CH:3]=[C:4]([C:10]2[C:11]([CH3:17])=[N:12][O:13][CH:14]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH3:9]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 54125846HCID 54125846, compound

Product 1

HCID 53859083HCID 53859083, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 4-(3-bromo-4-methoxyphenyl)-5-methoxy-3-methyl-4,5-dihydroisoxazole (260 mg, 0.87 mmol) in 15 mL of a 5:1 mixture of ethanol and 12N aqueous HCl was heated at reflux overnight. After cooling to room temperature, the reaction was concentrated to a small volume in vacuo. Saturated aqueous sodium bicarbonate (50 mL) was added and the mixture was extracted with 3×50 mL of ethyl acetate. The combined ethyl acetate layers were washed with 50 mL of brine, dried over sodium sulfate, and evaporated. The crude residue was subjected to flash chromatography on 25 g of silica gel eluting with 500 mL of 20% of diethyl ether/hexane to give 4-(3-bromo-4-methoxyphenyl)-3-methylisoxazole (158 mg, 68% yield) as a white solid. 1H NMR (400 MHz, CDCl3): δ 8.40 (s, 1H), 7.57 (d, 1H, J=2 Hz), 7.29 (dd, 1H, J=9, 2 Hz), 6.86 (d, 1H, J=9 Hz), 3.94 (s, 3H), 2.40 (s, 3H). Mass spectrum (ESI): m/e=268 (M+1).

Workup

  1. temperaturewas heated
  2. temperatureat reflux overnight
  3. concentrationthe reaction was concentrated to a small volume in vacuo
  4. additionSaturated aqueous sodium bicarbonate (50 mL) was added
  5. extractionthe mixture was extracted with 3×50 mL of ethyl acetate
  6. washThe combined ethyl acetate layers were washed with 50 mL of brine
  7. dry with materialdried over sodium sulfate
  8. customevaporated

Sources & evidence

ORD record
ord-7ab49fa0157549848f3ee9ff8dfb6a6f
Source dataset
uspto-grants-1999_03
Patent number
US05877191

Reaction notes

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