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

HRID 962809ノート

反応式

HRID 962809 の反応式
[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]

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 1118Sulfuric Acid溶媒2 回

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-c9fd011a7f654a94857c7e64b0138ac0
出典データセット
uspto-grants-1998_06
特許番号
US05760070

反応ノート

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