1-(2-Chloroethoxy)-2,6-dibromo-4-fluoro-3-nitrobenzene → 1-(2-Chloroethoxy)-4-fluoro-3-aminobenzene

HRID 1858367Notes

Reaction equation

HRID 1858367 reaction equation
[Cl:1][CH2:2][CH2:3][O:4][C:5]1[C:10](Br)=[CH:9][C:8]([F:12])=[C:7]([N+:13]([O-])=O)[C:6]=1Br>C(O)C.[Pd]>[Cl:1][CH2:2][CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([F:12])=[C:7]([NH2:13])[CH:6]=1

Participants

4

Reactant 1

HCID 105716291-(2-Chloroethoxy)-2,6-dibromo-4-fluoro-3-nitrobenzene

Product 1

HCID 105838151-(2-Chloroethoxy)-4-fluoro-3-aminobenzeneYield 90.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 1-(2-chloroethoxy)-2,6-dibromo-4-fluoro-3-nitrobenzene (73.2 g, 0.19 mol) in ethanol (1.1 L) containing 7.3 g of 10% palladium on carbon was hydrogenated at 40 psi for 5 days. The catalyst was filtered and the solvent was removed. The residue was dissolved in diethyl ether (300 ml) and washed with saturated aqueous sodium carbonate (200 ml). The organic layer was separated and washed with water, dried over anhydrous magnesium sulfate and filtered. The solvent was removed to afford an oil which solidified to afford 32.5 g (90.0%) of product as a dark solid: mp 42-43° C.; MS EI m/e 189/191 (M+); 1H NMR (CDCl3) δ3.40-3.60 (2H, bs, NH2), 3.77 (2H, d, J=6 Hz), 4.14 (2H, d, J=6 Hz), 6.19-6.23 (1 H, m), 6.36 (1H, dd, J=7, 3 Hz), 6.88 (1H, dd, J=11, 9 Hz).

Workup

  1. filtrationThe catalyst was filtered
  2. customthe solvent was removed
  3. dissolutionThe residue was dissolved in diethyl ether (300 ml)
  4. washwashed with saturated aqueous sodium carbonate (200 ml)
  5. customThe organic layer was separated
  6. washwashed with water
  7. dry with materialdried over anhydrous magnesium sulfate
  8. filtrationfiltered
  9. customThe solvent was removed
  10. customto afford an oil which

Sources & evidence

ORD record
ord-dac9aa4b5f5843ecbf704066bcada9f0
Source dataset
uspto-grants-2000_11
Patent number
US06150533

Reaction notes

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