Potassium Iodide → Methyl 5-Benzyloxy-4-methoxy-2-nitrobenzoate

HRID 1917817노트

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HRID 1917817 반응식
[OH:1][C:2]1[C:3]([O:15][CH3:16])=[CH:4][C:5]([N+:12]([O-:14])=[O:13])=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8].[CH2:17](Cl)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.C([O-])([O-])=O.[K+].[K+].[I-].[K+]>CN(C=O)C>[CH2:17]([O:1][C:2]1[C:3]([O:15][CH3:16])=[CH:4][C:5]([N+:12]([O-:14])=[O:13])=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

참가 물질

6

반응물 4

HCID 4875Potassium IodideHCID 7503Benzyl ChlorideHCID 11430Potassium CarbonateHCID 53396387Methyl 5-hydroxy-4-methoxy-2-nitrobenzoate

생성물 1

HCID 22667156Methyl 5-Benzyloxy-4-methoxy-2-nitrobenzoate수율 77.1%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
92.5 °C

실험 절차

To solution of methyl 5-hydroxy-4-methoxy-2-nitrobenzoate (13.0 g, 0.0572 mol) in DMF (120 mL) and benzyl chloride (7.23 ml, 0.0629 mol), K2CO3 (8.69 g, 0.0629 mol) and potassium iodide (0.949 g, 0.0057 mol) were added. The reaction mixture was heated at 90-95° C. overnight. The solvent was evaporated under vacuum and the residue was taken in ethyl acetate and washed with water and brine. After drying over MgSO4, the solution was concentrated ad purified on silica gel column to yield methyl 5-(benzyloxy)-4-methoxy-2-nitrobenzoate (13.99 g, 77% yield). 1HNMR (DMSO-d6): δ 7.66 (1H, s), 7.40 (6H, m), 5.27 (2H, s), 3.83 (3H, s), 3.80 (3H, s). LC-MS (ESI) m/z 318 (M+H)+.

후처리

  1. customThe solvent was evaporated under vacuum
  2. washwashed with water and brine
  3. dry with materialAfter drying over MgSO4
  4. concentrationthe solution was concentrated ad
  5. custompurified on silica gel column

출처 및 근거

ORD 기록
ord-1433d64ff88c449d9ec941759dd1a7db
출처 데이터셋
uspto-grants-2013_12
특허 번호
US08618289B2

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