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

HRID 399012Notes

Reaction equation

HRID 399012 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 separated and washed with water, dried over anhydrous magnesium sulfate, filtered, and the solvent removed to afford an oil which solidies to afford 32.5 g (90.0%) a dark solid: mp 42°-43° C.; MS EI m/e 189/191 (M+); 1H NMR (CDCl3) δ 3.40-3.60 (2H, bs, NH2), 3.77 (2H, d, J=6 Hz), 4.14 (2H, d, J=6 Hz), 6.19-6.23 (1H, 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 separated
  6. washwashed with water
  7. dry with materialdried over anhydrous magnesium sulfate
  8. filtrationfiltered
  9. customthe solvent removed
  10. customto afford an oil which

Sources & evidence

ORD record
ord-15f7c081111b4a70be003d016246ccf2
Source dataset
uspto-grants-1998_10
Patent number
US05817690

Reaction notes

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