HCID 18786094, compound → HCID 18786085, compound

HRID 1107847Notes

Reaction equation

HRID 1107847 reaction equation
[Br-:1].[F:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][P+:10]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[C:5]([N+:29]([O-])=O)[CH:4]=1>CCO.Br.[Zn]>[Br-:1].[NH2:29][C:5]1[CH:4]=[C:3]([F:2])[CH:8]=[CH:7][C:6]=1[CH2:9][P+:10]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)([C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

5

Reactant 1

HCID 18786094HCID 18786094, compound

Product 1

HCID 18786085HCID 18786085, compoundYield 54.5%

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 260Hydrogen BromideSolventHCID 702EthanolSolvent

Procedure

A solution of 175 g (0.35 mol) of [(4-fluoro-2-nitrophenyl)methyl]-triphenylphosphonium bromide in 760 mL of EtOH and 380 mL of 48% HBr was brought to reflux and 138 g (2.1 mol) of zinc dust was added in portions over 4 h and refluxed further for 2 h. The mixture was cooled and the EtOH evaporated. The residue was partitioned between CH2Cl2 and H2O. The CH2Cl2 solution was washed with 7M NH4OH. The aqueous phase was decanted and the precipitate dissolved in CH2Cl2 /EtOH. The organic phase was washed with brine, dried (Na2SO4) and concentrated. There was obtained 89 g (54%) of [(2-amino-4-fluorophenyl)methyl]triphenylphosphonium bromide as a solid: 1H NMR (Me2SO-d6) δ 8.0-7.6 (m, 15H); 6.6 (m, 1H); 6.4 (m, 1H); 6.15 (m, 1H); 5.5 (br s, 2H); 4.95 (d, 2H). ##STR17##

Workup

  1. temperatureto reflux
  2. temperaturerefluxed further for 2 h
  3. temperatureThe mixture was cooled
  4. customthe EtOH evaporated
  5. customThe residue was partitioned between CH2Cl2 and H2O
  6. washThe CH2Cl2 solution was washed with 7M NH4OH
  7. customThe aqueous phase was decanted
  8. dissolutionthe precipitate dissolved in CH2Cl2 /EtOH
  9. washThe organic phase was washed with brine
  10. dry with materialdried (Na2SO4)
  11. concentrationconcentrated

Sources & evidence

ORD record
ord-d66eb1048e464c5b8e4634355419d595
Source dataset
uspto-grants-2000_05
Patent number
US06063803

Reaction notes

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