Hydrochloric Acid → 3-Pyridinemethanol, 2-bromo-alpha-(2-chlorophenyl)-

HRID 2251954노트

반응식

HRID 2251954 반응식
[Li+].CC([N-]C(C)C)C.[Br:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][N:11]=1.[Cl:16][C:17]1[CH:24]=[CH:23][CH:22]=[CH:21][C:18]=1[CH:19]=[O:20].Cl>C1COCC1>[Br:9][C:10]1[C:15]([CH:19]([C:18]2[CH:21]=[CH:22][CH:23]=[CH:24][C:17]=2[Cl:16])[OH:20])=[CH:14][CH:13]=[CH:12][N:11]=1

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 69962-ChlorobenzaldehydeHCID 79732-BromopyridineHCID 2724682Lithium diisopropylamide

생성물 1

HCID 866012413-Pyridinemethanol, 2-bromo-alpha-(2-chlorophenyl)-

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

Add LDA (400 mL, 0.8 mol) to 2-bromopyridine (105 g, 0.667 mol) in THF (3.2 L) at −78° C. and stir. After 2 hours, add 2-chlorobenzaldehyde (103 g, 0.733 mol) in THF (300 mL) and allow the reaction mixture to gradually warm to ambient temperature. Treat the reaction mixture with 1 M HCl (1.7 L) and extract with diethyl ether. Combine the organic layers and wash with water and brine. Dry over sodium sulfate, filter, and concentrate under reduced pressure. Purification by flash chromatography, eluting with hexane:ethyl acetate (10:1 to 1:1) gives the title compound: 1H NMR (300 MHz, CDCl3), δ8.28(dd, 1H, J=1.83, 4.73), 7.67 (dd, 1H, J=1.83, 7.63), 7.48-7.19 (m, 5H), 6.41 (s, 1H), 3.10 (bs, 1H); MS (IS) m/z 298.0 (M+1), 300.0 (M+1); Analysis for C12H9BrClNO: calcd: C, 48.27; H, 3.04; N, 4.69; found: C, 49.06; H, 3.18; N, 4.64. Rf=0.29 heptane: ethyl acetate, 2:1).

후처리

  1. extractionextract with diethyl ether
  2. washwash with water and brine
  3. dry with materialDry over sodium sulfate
  4. filtrationfilter
  5. concentrationconcentrate under reduced pressure
  6. customPurification by flash chromatography
  7. washeluting with hexane:ethyl acetate (10:1 to 1:1)

출처 및 근거

ORD 기록
ord-a9949d77e28042d4a6cc230155e38c81
출처 데이터셋
uspto-grants-2008_01
특허 번호
US07320994B2

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