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

HRID 962809노트

반응식

HRID 962809 반응식
[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]

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 1118Sulfuric Acid용매2회

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-c9fd011a7f654a94857c7e64b0138ac0
출처 데이터셋
uspto-grants-1998_06
특허 번호
US05760070

반응 노트

불러오는 중…