Triphenylphosphine → 2-(5-Bromopent-1-ynyl)pyridine

HRID 334634노트

반응식

HRID 334634 반응식
[Br:1]Br.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[N:22]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1[C:28]#[C:29][CH2:30][CH2:31][CH2:32]O>C(Cl)Cl>[Br:1][CH2:32][CH2:31][CH2:30][C:29]#[C:28][C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][N:22]=1

참가 물질

5

반응물 3

HCID 11776TriphenylphosphineHCID 24408BromineHCID 109973535-(Pyridin-2-yl)pent-4-yn-1-ol

생성물 1

HCID 665979292-(5-Bromopent-1-ynyl)pyridine수율 29%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

반응 조건

온도
5 °C

실험 절차

Br2 (1.11 mL, 21.4 mmol) was added to a solution of triphenylphosphine (8.30 g, 30.7 mmol) in DCM (40 mL) at −5° C. A solution of 5-pyridin-2-yl-pent-4-yn-1-ol (3.00, 18.6 mmol) in DCM (10 mL) was added dropwise to the reaction mixture in order to maintain a temperature lower than 5° C. The reaction mixture was stirred for 5 hours at −10° C. and was quenched with a saturated solution of NaHCO3. The aqueous phase was extracted with DCM. The resulting organic phase was washed with brine, dried over MgSO4, filtered and evaporated. The crude residue was purified by flash chromatography (DCM/MeOH 99.5:0.5) to yield 2-(5-bromo-pent-1-ynyl)-pyridine (1.20 g, 5.35 mmol, 29%) with a purity of 50%.

후처리

  1. customwas quenched with a saturated solution of NaHCO3
  2. extractionThe aqueous phase was extracted with DCM
  3. washThe resulting organic phase was washed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customevaporated
  7. customThe crude residue was purified by flash chromatography (DCM/MeOH 99.5:0.5)

출처 및 근거

ORD 기록
ord-9313c62210014996a25cb65f7ca1bee0
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08883826B2

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