Nitric Acid → HCID 68986110, compound

HRID 1257187Notes

Reaction equation

HRID 1257187 reaction equation
[N+:1]([O-:4])(O)=[O:2].[Br:5][C:6]1[CH:11]=[C:10]([F:12])[CH:9]=[CH:8][C:7]=1[CH2:13][C:14]([OH:16])=[O:15]>>[Br:5][C:6]1[CH:11]=[C:10]([F:12])[C:9]([N+:1]([O-:4])=[O:2])=[CH:8][C:7]=1[CH2:13][C:14]([OH:16])=[O:15]

Participants

3

Reactant 2

HCID 944Nitric AcidHCID 34778092-Bromo-4-fluorophenylacetic acid

Product 1

HCID 68986110HCID 68986110, compoundYield 92%

Conditions

Temperature
5 °C

Procedure

Nitric acid (16.00 mL, 322 mmol) was cooled to −15° C. and treated portion-wise with 2-bromo-4-fluorophenylacetic acid (10.00 g, 42.9 mmol) maintaining an internal temperature of −10° C. to −5° C. Once the addition was complete the mixture was warmed to 5° C. over −15 minutes, poured onto ice (200 mL), stirred vigorously until all of the ice melted, and then filtered and rinsed with water. The resulting solid was dissolved in EtOAc, washed with brine, dried (MgSO4) and concentrated to dryness to afford 2-(2-bromo-4-fluoro-5-nitrophenyl)acetic acid (10.93 g, 92% yield) as a bright yellow solid. 1H NMR (400 MHz, DMSO-d6): δ 8.29 (d, 1H), 8.04 (d, 1H), 3.85 (s, 2H).

Workup

  1. temperaturemaintaining an internal temperature of −10° C. to −5° C
  2. additionOnce the addition
  3. additionpoured onto ice (200 mL)
  4. filtrationfiltered
  5. washrinsed with water
  6. dissolutionThe resulting solid was dissolved in EtOAc
  7. washwashed with brine
  8. dry with materialdried (MgSO4)
  9. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-97a97a3251484f228a4637b64ab963a7
Source dataset
uspto-grants-2013_06
Patent number
US08461179B1

Reaction notes

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