Phenol → 2-Bromo-6-phenoxypyridine

HRID 2309227노트

반응식

HRID 2309227 반응식
[H-].[Na+].[C:3]1([OH:9])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[Br:10][C:11]1[CH:16]=[CH:15][CH:14]=[C:13](Br)[N:12]=1>CN(C)C=O>[Br:10][C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([O:9][C:3]2[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=2)[N:12]=1

참가 물질

5

반응물 3

HCID 996PhenolHCID 122742,6-DibromopyridineHCID 24758Sodium hydride

생성물 1

HCID 8245892-Bromo-6-phenoxypyridine수율 79%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매2회

실험 절차

To a solution of 6.5 g (0.135 mol) of 50% sodium hydride in 75 ml of dimethylformamide at 0° C. and under N2 was added a solution of 11.9 g (0.127 mol) of phenol in 75 ml of dimethylformamide. Once dropwise addition was complete, 30.0 g (0.127 mol) of 2,6-dibromopyridine was added in one portion and the mixture was heated at 60° to 65° C. for 18 hours. The mixture was then cooled and partitioned between ether and 1N aqueous NaOH. The ether extracts were washed two times with aqueous NaHCO3, dried over MgSO4, filtered and concentrated under vacuum. The solid residue was slurried in hexane, filtered and dried to afford 25.1 g (79%) of the title compound as a white powder: m.p. 83° to 86° C.; 1H NMR (CDCl3) δ 6.70 (d, 1H), 7.0-7.5 (m, 7 H).

후처리

  1. additionOnce dropwise addition
  2. temperaturethe mixture was heated at 60° to 65° C. for 18 hours
  3. temperatureThe mixture was then cooled
  4. custompartitioned between ether and 1N aqueous NaOH
  5. washThe ether extracts were washed two times with aqueous NaHCO3
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated under vacuum
  9. filtrationfiltered
  10. customdried

출처 및 근거

ORD 기록
ord-1fb4efaaa6594a2faa84b2f54c993cdb
출처 데이터셋
uspto-grants-1987_09
특허 번호
US04694013

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