Ammonium Chloride → HCID 86713632, compound

HRID 1257189Notes

Reaction equation

HRID 1257189 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([F:8])[C:5]([N+:9]([O-])=O)=[CH:4][C:3]=1[CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14].[Cl-].[NH4+]>CCO.[Fe]>[NH2:9][C:5]1[C:6]([F:8])=[CH:7][C:2]([Br:1])=[C:3]([CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH:4]=1

Participants

5

Reactant 2

HCID 25517Ammonium ChlorideHCID 68984776HCID 68984776, compound

Product 1

HCID 86713632HCID 86713632, compoundYield 93.4%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 702EthanolSolvent

Conditions

Temperature
55 °C

Procedure

A solution of ethyl 2-(2-bromo-4-fluoro-5-nitrophenyl)acetate (2.127 g, 6.95 mmol) in EtOH (70 mL) was treated with iron powder (3.88 g, 69.5 mmol) and satd ammonium chloride (14.48 mL, 69.5 mmol) and heated to 55° C. for 1 h. The mixture was cooled to RT, filtered through a pad of diatomaceous earth, rinsed well with EtOH and the organics concentrated under reduced pressure. The resulting aqueous residue was treated with satd. NaHCO3, extracted with EtOAc (2×) and the combined organics were washed with water, dried (MgSO4), and concentrated to afford ethyl 2-(5-amino-2-bromo-4-fluorophenyl)acetate (1.792 g, 93% yield) as an amber oil. 1H NMR (400 MHz, DMSO-d6): δ 7.25 (d, 1H), 6.76 (d, 1H), 5.35 (s, 2H), 4.08 (q, 2H), 3.61 (s, 2H), 1.18 (t, 3H); MS (ESI) m/z: 278.0 [M+H]+.

Workup

  1. temperatureThe mixture was cooled to RT
  2. filtrationfiltered through a pad of diatomaceous earth
  3. washrinsed well with EtOH
  4. concentrationthe organics concentrated under reduced pressure
  5. additionThe resulting aqueous residue was treated with satd
  6. extractionNaHCO3, extracted with EtOAc (2×)
  7. washthe combined organics were washed with water
  8. dry with materialdried (MgSO4)
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-01a5b211aa34456a8e6a1ab45797353d
Source dataset
uspto-grants-2013_06
Patent number
US08461179B1

Reaction notes

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