Nitric Acid → HCID 68986110, compound

HRID 522730Notes

Reaction equation

HRID 522730 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]>S(=O)(=O)(O)O>[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

4

Reactant 2

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

Product 1

HCID 68986110HCID 68986110, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Conditions

Temperature
-5 °C

Procedure

Add nitric acid (65%, 21.0 g, 0.22 mol) dropwise to a cooled mixture (−10° C.) of (2-bromo-4-fluorophenyl)acetic acid (50 g, 0.22 mol) in concentrated sulfuric acid (250 mL) and stir the resulting mixture at −10-0° C. for 20 min. Pour onto crushed ice, extract with EtOAc (3×200 mL), wash organics with brine (3×100 mL), dry over sodium sulfate, and concentrate in vacuo to give the title compound (50 g, 84% yield). 1H NMR (400 MHz, CDCl3): δ 8.04 (d, J=7.6 Hz, 1H), 7.57 (d, J=9.0 Hz, 1H), 3.87 (s, 2H).

Workup

  1. additionPour
  2. customonto crushed ice
  3. extractionextract with EtOAc (3×200 mL)
  4. washwash organics with brine (3×100 mL)
  5. dry with materialdry over sodium sulfate
  6. concentrationconcentrate in vacuo

Sources & evidence

ORD record
ord-a948b09d9b4b483682234e3863e399e5
Source dataset
uspto-grants-2016_05
Patent number
US09334267B2

Reaction notes

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