HCID 89814045, compound → 1-(5-Amino-2-bromo-4-fluorophenyl)propan-2-one

HRID 522732Notes

Reaction equation

HRID 522732 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])[CH3:14]>C(O)(=O)C.[Fe]>[NH2:9][C:5]1[C:6]([F:8])=[CH:7][C:2]([Br:1])=[C:3]([CH2:12][C:13](=[O:15])[CH3:14])[CH:4]=1

Participants

4

Reactant 1

HCID 89814045HCID 89814045, compound

Product 1

HCID 898138911-(5-Amino-2-bromo-4-fluorophenyl)propan-2-oneYield 95.1%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 176Acetic AcidSolvent

Conditions

Temperature
50 °C

Procedure

Treat a mixture of 1-(2-bromo-4-fluoro-5-nitrophenyl)propan-2-one (12 g, 43.6 mmol) in acetic acid (200 mL) with iron powder (24 g, 0.436 mol) and stir at 50° C. for 1 h. Add water and EtOAc, filter to remove solids, and extract the filtrate with EtOAc (2×). Wash the combined organics with saturated. Na2CO3, then brine, dry over Na2SO4 and concentrate to dryness to afford the title compound (10.2 g, 94% yield). 1H NMR (400 MHz, DMSO-d6): δ 7.26 (d, J=10.8 Hz, 1H), 6.69 (d, J=9.6 Hz, 1H), 5.33 (s, 2H), 3.74 (s, 2H), 2.14 (s, 3H).

Workup

  1. additionTreat
  2. filtrationAdd water and EtOAc, filter
  3. customto remove solids
  4. extractionextract the filtrate with EtOAc (2×)
  5. washWash the combined organics with saturated
  6. dry with materialNa2CO3, then brine, dry over Na2SO4
  7. concentrationconcentrate to dryness

Sources & evidence

ORD record
ord-d782e21649ec42ed9bad30602050b120
Source dataset
uspto-grants-2016_05
Patent number
US09334267B2

Reaction notes

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