Dichloromethane → 4-Bromo-5-nitrothiophene-2-carbaldehyde

HRID 723228

반응식

HRID 723228 반응식
[N+:1]([O-:4])([O-])=[O:2].[K+].[Br:6][C:7]1[CH:8]=[C:9]([CH:12]=[O:13])[S:10][CH:11]=1.C(Cl)Cl>OS(O)(=O)=O>[Br:6][C:7]1[CH:8]=[C:9]([CH:12]=[O:13])[S:10][C:11]=1[N+:1]([O-:4])=[O:2]

참가 물질

5

반응물 3

HCID 6344DichloromethaneHCID 24434Potassium NitrateHCID 877924-Bromothiophene-2-carbaldehyde

생성물 1

HCID 218862814-Bromo-5-nitrothiophene-2-carbaldehyde수율 98.6%

시약·촉매·용매 1

HCID 1118Sulfuric Acid용매2회

반응 조건

온도
0 °C

실험 절차

A solution of potassium nitrate (110 g, 1.09 mol) in H2SO4 (550 mL, conc.) was added to a solution of 4-bromo-thiophene-2-carbaldehyde (207.6 g, 1.08 mol) in H2SO4 (1.1 L, conc.) at CH2Cl2 (5 mL, anhydrous) at 0° C. over a 45 minute period. The reaction mixture was stirred 0° C. for 2 hrs, then stirred overnight at rt. The reaction mixture was poured over ice, filtered, and washed with water and hexanes. The yellow solid was dried overnight to afford the title compound (251.4 g, 98.6%). 1H-NMR (DMSO-d6): δ 9.90 (s, 1H), 8.56 (s, 1H).

후처리

  1. stirringstirred overnight at rt
  2. additionThe reaction mixture was poured over ice
  3. filtrationfiltered
  4. washwashed with water and hexanes
  5. customThe yellow solid was dried overnight

출처 및 근거

ORD 기록
ord-d103f6c77f19491694048527fd202014
출처 데이터셋
uspto-grants-2006_11
특허 번호
US07138530B2

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