Nitric Acid → HCID 68759685, compound

HRID 1804706Notes

Reaction equation

HRID 1804706 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[CH:10][C:6]([CH2:7][CH2:8][Br:9])=[CH:5][CH:4]=1.[N+:12]([O-])([OH:14])=[O:13]>FC(F)(F)C(O)=O>[Br:9][CH2:8][CH2:7][C:6]1[CH:10]=[CH:11][C:3]([O:2][CH3:1])=[C:4]([N+:12]([O-:14])=[O:13])[CH:5]=1

Participants

4

Reactant 2

HCID 944Nitric Acid2×HCID 844271-(2-Bromoethyl)-4-methoxybenzene

Product 1

HCID 68759685HCID 68759685, compound

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent2×

Conditions

Temperature
0 °C

Procedure

Into a 500 mL pear flask was charged 4-methoxyphenethyl bromide (0.727 ml, 4.65 mmol) in trifluoroacetic acid (9.30 ml). The solution was cooled to 0° C. In a 50 mL Erlenmeyer flask was added nitric acid (0.231 ml, 4.65 mmol) and trifluoroacetic acid (2.0 mL). The nitric acid solution was added to the reaction dropwise via syringe. The reaction was stirred at room temperature for 2 hours. The solvent was removed on a rotovap and the residue taken up into ethyl acetate. The reaction was washed with 1N HCl, saturated aqueous sodium bicarbonate, and brine, dried over MgSO4, filtered and concentrated onto silica gel. The reaction was purified by flash chromatography (10% ethyl acetate:hexanes for 20 minutes, then to 50% ethyl acetate:hexanes over 20 minutes) to provide the title compound. MS (DCI) m/e 277 (M+NH4).

Workup

  1. customThe solvent was removed on a rotovap
  2. washThe reaction was washed with 1N HCl, saturated aqueous sodium bicarbonate, and brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated onto silica gel
  6. customThe reaction was purified by flash chromatography (10% ethyl acetate
  7. waithexanes for 20 minutes

Sources & evidence

ORD record
ord-c1d9a4395ce24b279c5c05a834aaa9db
Source dataset
uspto-grants-2013_01
Patent number
US08354422B2

Reaction notes

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