Propionitrile → 2-Bromo-4-phenylpyridine

HRID 33477

반응식

HRID 33477 반응식
[C:1]1([C:7]2[CH:12]=[CH:11][N:10]=[C:9](C=O)[CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(#N)CC.C[Si]([Br:23])(C)C.[OH-].[Na+]>>[Br:23][C:9]1[CH:8]=[C:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH:12]=[CH:11][N:10]=1

참가 물질

5

반응물 4

HCID 7854PropionitrileHCID 14798Sodium HydroxideHCID 76113BromotrimethylsilaneHCID 122176544-Phenylpyridine-2-carboxaldehyde

생성물 1

HCID 1047002-Bromo-4-phenylpyridine

실험 절차

4-Phenyl-pyridine-2-carbaldehyde: To a clear, colorless solution of 1A (0.850 g, 4.5 mmol) in propionitrile (4.5 mmol) was added trimethylsilyl bromide (2.95 mL, 22.4 mmol). The resulting orange suspension was microwaved in a sealed tube at 150° C. for 10 min. The reaction was cooled to rt and poured into 1.0 N NaOH containing ice. The aqueous layer was extracted with diethyl ether (2×). The combined organic layers were washed with sat. NaHCO3, brine, dried over Na2SO4, filtered and concentrated to give 1.07 g of 2-bromo-4-phenyl pyridine as an off-white solid. MS 233.9 (M+H)+ and 235.9 (M+2+H)+.

후처리

  1. customThe resulting orange suspension was microwaved in a sealed tube at 150° C. for 10 min
  2. additioncontaining ice
  3. extractionThe aqueous layer was extracted with diethyl ether (2×)
  4. washThe combined organic layers were washed with sat. NaHCO3, brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated

출처 및 근거

ORD 기록
ord-9db78dd831754311a32348aedf68589c
출처 데이터셋
uspto-grants-2008_09
특허 번호
US07429604B2

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