Acetic Acid → 2-Iodo-4,5-dimethoxybenzaldehyde

HRID 1647023

반응식

HRID 1647023 반응식
C[O:2][CH:3](OC)[C:4]1[CH:9]=[C:8]([O:10][CH3:11])[C:7]([O:12][CH3:13])=[CH:6][C:5]=1Br.C([Li])CCC.[I:22]I.C(O)(=O)C>O1CCCC1>[I:22][C:5]1[CH:6]=[C:7]([O:12][CH3:13])[C:8]([O:10][CH3:11])=[CH:9][C:4]=1[CH:3]=[O:2]

참가 물질

6

반응물 4

HCID 176Acetic AcidHCID 807IodineHCID 110771461-Bromo-2-(dimethoxymethyl)-4,5-dimethoxybenzeneHCID 178418339Butyllithium

생성물 1

HCID 110117632-Iodo-4,5-dimethoxybenzaldehyde수율 72.7%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

반응 조건

온도
-70 °C

실험 절차

2-Bromo-4,5-dimethoxybenzaldehyde dimethylacetal (59 g) is dissolved in tetrahydrofuran and thereto is added 2.5M n-butyllithium (89 ml) under cooling at -70° C. The reaction mixture is kept below -50° C. for 30 minutes and thereto is added dropwise a solution of iodine (51.4 g) in tetrahydrofuran below -50° C. The mixture is kept at the same temperature for 15 minutes and thereto are added aqueous acetic acid to adjust the pH of the solution at 2. The mixture is allowed to stand at room temperature overnight, and the solvent is distilled off from the reaction mixture. The residue is dissolved in ethyl acetate. The solution is washed and dried, and the solvent is distilled off. The residue is crystallized from ethyl acetate to give 2-iodo-4,5-dimethoxybenzaldehyde (43 g). M.p. 139°-141° C.

후처리

  1. waitThe mixture is kept at the same temperature for 15 minutes
  2. waitto stand at room temperature overnight
  3. distillationthe solvent is distilled off from the reaction mixture
  4. dissolutionThe residue is dissolved in ethyl acetate
  5. washThe solution is washed
  6. customdried
  7. distillationthe solvent is distilled off
  8. customThe residue is crystallized from ethyl acetate

출처 및 근거

ORD 기록
ord-8235fb7619db4759bef295f68cdaa723
출처 데이터셋
uspto-grants-1993_01
특허 번호
US05182404

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