Benzyl Bromide → 4-(Benzyloxy)-2-bromopyridine

HRID 523918노트

반응식

HRID 523918 반응식
[H-].[Na+].[Br:3][C:4]1[CH:9]=[C:8]([OH:10])[CH:7]=[CH:6][N:5]=1.[CH2:11](Br)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.CCOC(C)=O>CN(C=O)C>[CH2:11]([O:10][C:8]1[CH:7]=[CH:6][N:5]=[C:4]([Br:3])[CH:9]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

참가 물질

6

반응물 4

HCID 7498Benzyl BromideHCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 178516474HCID 178516474, 화합물

생성물 1

HCID 153891994-(Benzyloxy)-2-bromopyridine수율 51.2%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

NaH (761 mg, 19.83 mmol) was added portion wise to 2-bromo-4-hydroxypyridine (3 g, 17.24 mmol) in DMF (50 mL) at 0° C. under Ar(g). Then the reaction mixture was stirred at rt for 10 min after which it was again cooled down at 0° C. and benzyl bromide (2.15 mL, 18.10 mmol) was added. The reaction was stirred at it for 4 h, after which it was poured onto brine (200 mL) and EtOAc (200 mL) was added. The phases were separated and the organic phase was dried over MgSO4, filtered and subsequently evaporated under reduced pressure. The resulting residue was purified by silica gel column chromatography eluting with hexane/EtOAc (90:10 to 80:20) to furnish I as a white solid (2.331 g, 51%).

후처리

  1. temperaturewas again cooled down at 0° C.
  2. stirringThe reaction was stirred at it for 4 h
  3. additionwas added
  4. customThe phases were separated
  5. dry with materialthe organic phase was dried over MgSO4
  6. filtrationfiltered
  7. customsubsequently evaporated under reduced pressure
  8. customThe resulting residue was purified by silica gel column chromatography
  9. washeluting with hexane/EtOAc (90:10 to 80:20)

출처 및 근거

ORD 기록
ord-2bffd9e2d85942cbb70d04b1477d6fef
출처 데이터셋
uspto-grants-2016_05
특허 번호
US09340503B2

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