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Water → Methyl 3-(benzyloxy)-4,6-dibromopicolinate

HRID 49428
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HRID 49428 반응식
[H-].[Na+].[Br:3][C:4]1[CH:9]=[C:8]([Br:10])[N:7]=[C:6]([C:11]([O:13][CH3:14])=[O:12])[C:5]=1[OH:15].[CH2:16](Cl)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.O>CN(C=O)C>[Br:3][C:4]1[CH:9]=[C:8]([Br:10])[N:7]=[C:6]([C:11]([O:13][CH3:14])=[O:12])[C:5]=1[O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1
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참가 물질

6

반응물 4

HCID 962WaterHCID 7503Benzyl ChlorideHCID 24758Sodium hydrideHCID 22175130Methyl 4,6-dibromo-3-hydroxypicolinate

생성물 1

HCID 22175074Methyl 3-(benzyloxy)-4,6-dibromopicolinate수율 90.6%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a stirred mixture of sodium hydride (0.6 g) in DMF (50 mL) was slowly added 14 (7.1 g). After the addition was complete, the mixture was stirred at room temperature for 15 minutes, then benzyl chloride (3.05 g) was added all at once. The mixture was then heated at 90° C. for six hours, cooled, poured into water (500 mL) and extracted with ether (2×200 mL). The ether extracts were combined, washed with 2N NaOH (50 mL), dried (MgSO4) and the solvent was evaporated to give 15 as a light yellow solid (8.3 g). Recrystallization from a small volume of methanol gave an analytical sample, m.p. 75-76° C.

후처리

  1. additionAfter the addition
  2. temperatureThe mixture was then heated at 90° C. for six hours
  3. temperaturecooled
  4. extractionextracted with ether (2×200 mL)
  5. washwashed with 2N NaOH (50 mL)
  6. dry with materialdried (MgSO4)
  7. customthe solvent was evaporated

출처 및 근거

ORD 기록
ord-89ae3bd4012e488db8e1fde26da28f53
출처 데이터셋
uspto-grants-2004_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06706740B2

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