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

HRID 962809Notes

Reaction equation

HRID 962809 reaction equation
[Cl:1][CH2:2][CH2:3][O:4][C:5]1[C:10]([Br:11])=[CH:9][C:8]([F:12])=[CH:7][C:6]=1[Br:13].[N+:14]([O-])([OH:16])=[O:15]>S(=O)(=O)(O)O>[Cl:1][CH2:2][CH2:3][O:4][C:5]1[C:6]([Br:13])=[CH:7][C:8]([F:12])=[C:9]([N+:14]([O-:16])=[O:15])[C:10]=1[Br:11]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 108304061,3-Dibromo-2-(2-chloroethoxy)-5-fluorobenzene

Product 1

HCID 105716291-(2-Chloroethoxy)-2,6-dibromo-4-fluoro-3-nitrobenzeneYield 97.1%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent2×

Procedure

To a solution of 1-(2-chloroethoxy)-2,6-dibromo-4-fluorobenzene (65.8 g, 0.20 mol) in concentrated sulfuric acid (165 mL) maintained at room temperature using a water bath was slowly added a solution of nitric acid in sulfuric acid (10 mL HNO3 in 165 mL H2SO4). The reaction was allowed to stir at room temperature for 1 hour then poured into ice (1.5 L) and extracted with methylene chloride (2×300 mL). The combined organic layers were washed with aqueous sodium bicarbonate (150 mL) and dried over anhydrous magnesium sullfate, filtered, and the solvent removed under vacuum to afford 73.3 g (97.1%) a white crystalline solid: mp 56°-57 MS EI m/e 375/377/379/381; 1H NMR (CDCl3) δ 3.91 (2H, t, J=5.9 Hz), 4.29 (2H, d, J=5.9 Hz), 7.54 (8.1 Hz).

Workup

  1. extractionextracted with methylene chloride (2×300 mL)
  2. washThe combined organic layers were washed with aqueous sodium bicarbonate (150 mL)
  3. dry with materialdried over anhydrous magnesium sullfate
  4. filtrationfiltered
  5. customthe solvent removed under vacuum

Sources & evidence

ORD record
ord-c9fd011a7f654a94857c7e64b0138ac0
Source dataset
uspto-grants-1998_06
Patent number
US05760070

Reaction notes

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