Nitric Acid → 2,5-Dichloro-3-nitrobenzoic acid

HRID 1043712

반응식

HRID 1043712 반응식
[Cl:1][C:2]1[CH:10]=[CH:9][C:8]([Cl:11])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[N+:12]([O-])([OH:14])=[O:13]>OS(O)(=O)=O>[Cl:1][C:2]1[C:10]([N+:12]([O-:14])=[O:13])=[CH:9][C:8]([Cl:11])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5]

참가 물질

4

반응물 2

HCID 944Nitric AcidHCID 57842,5-Dichlorobenzoic acid

생성물 1

HCID 69512,5-Dichloro-3-nitrobenzoic acid수율 95.5%

시약·촉매·용매 1

HCID 1118Sulfuric Acid용매

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온도
0 °C

실험 절차

To a solution of 2,5-dichlorobenzoic acid (3 g, 15.7 mmol) in H2SO4 (16 mL) at 0° C. was added dropwise fuming nitric acid (1.4 mL, 31.4 mmol) and the reaction mixture was stirred for 5 minutes at 0° C., and was then gradually allowed to warm to over 20 minutes. The reaction was treated with ice water and extracted with EtOAc. The organic layer was washed with water and brine then dried (Na2SO4), filtered and concentrated to afford 3.54 g (48%) of 2,5-dichloro-3-nitrobenzoic acid which is contaminated with 3,6-dichloro-2-nitrobenzoic acid (40%): 1H NMR (300 MHz, CD3OD) δ 7.73 (s, 1H) 8.06 (d, J=2.6 Hz, 1H) 8.11 (d, J=2.6 Hz, 1H).

후처리

  1. temperatureto warm to over 20 minutes
  2. extractionextracted with EtOAc
  3. washThe organic layer was washed with water and brine
  4. dry with materialthen dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated

출처 및 근거

ORD 기록
ord-d595493b9c1c457481affc30beaafc60
출처 데이터셋
uspto-grants-2013_10
특허 번호
US08563553B2

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