Nitric Acid → HCID 68986110, compound

HRID 1930304Notes

Reaction equation

HRID 1930304 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 51%

Procedure

To stirring fuming HNO3 (15 mL) at −15° C. was added 2-bromo-4-fluorophenylacetic acid (10 g, 43 mmol) in portions such that the internal temperature remained below −10° C. After completing the addition the reaction was stirred with warming to +5° C. over 15 min. The mixture was poured onto ice (500 g). Product separated as a slightly sticky solid which on manipulation with a spatula became powdery. The suspension was stirred vigorously until the ice had completely melted. While still very cold, the solids were collected by filtration, rinsed very well with H2O (1 L). The solid was dried under vacuum to afford 2-(2-bromo-4-fluoro-5-nitrophenyl)acetic acid (6.04 g, 51% yield) as a pale yellow solid which was used as is in the next reaction.

Workup

  1. customremained below −10° C
  2. additionthe addition the reaction
  3. temperaturewith warming to +5° C. over 15 min
  4. additionThe mixture was poured onto ice (500 g)
  5. customProduct separated as a slightly sticky solid which on manipulation with a spatula
  6. stirringThe suspension was stirred vigorously until the ice
  7. filtrationWhile still very cold, the solids were collected by filtration
  8. washrinsed very well with H2O (1 L)
  9. customThe solid was dried under vacuum

Sources & evidence

ORD record
ord-368ac0e827be489a85bcb779f3b7135f
Source dataset
uspto-grants-2012_05
Patent number
US08188113B2

Reaction notes

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