Hydrochloric Acid → 3-(Pyridin-2-yl)benzaldehyde

HRID 48044노트

반응식

HRID 48044 반응식
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=1.[Li]CCCC.Br[C:14]1[CH:15]=[C:16]([CH:19]=[CH:20][CH:21]=1)[CH:17]=[O:18].Cl>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1COCC1>[N:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[C:14]1[CH:15]=[C:16]([CH:19]=[CH:20][CH:21]=1)[CH:17]=[O:18]

참가 물질

7

반응물 4

HCID 313Hydrochloric AcidHCID 79732-BromopyridineHCID 765833-BromobenzaldehydeHCID 178418339Butyllithium

생성물 1

HCID 37100393-(Pyridin-2-yl)benzaldehyde수율 38.2%

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매HCID 8028Tetrahydrofuran용매2회

반응 조건

온도
-78 °C

실험 절차

Ex-587A) To a THF solution (8 mL) of 2-bromopyridine (1.30 g, 8.23 mmol) at −78° C. was added 1.6 M n-BuLi in hexanes (5.3 mL, 8.48 mmol). The resulting dark red solution was stirred at −78° C. for 10 min, and a solution of 0.5 M ZnCI2 in THF (18 mL, 9.0 mmol) was added giving a light brown slurry. After warming to room temperature, 3-bromobenzaldehyde (0.816 mL, 7.0 mmol) and Pd(PPh3)4 (0.242 g, 0.21 mmol) were added, and the mixture was stirred for 18 h at room temperature under argon. The reaction mixture was poured into 1 N HCl (30 mL) and washed with diethyl ether. The aqueous layer was neutralized with NaHCO3 and extracted with diethyl ether. The solvent was removed in vacuo to give the crude product as an oil. Purification by flash chromatography on silica gel eluting with 20% ethyl acetate in hexane gave 0.49 g (38%) of the desired 3-(2-pyridinyl)benzaldehyde product as a colorless oil. GCMS: m/z=183 [M+].

후처리

  1. customgiving a light brown slurry
  2. temperatureAfter warming to room temperature
  3. stirringthe mixture was stirred for 18 h at room temperature under argon
  4. washwashed with diethyl ether
  5. extractionextracted with diethyl ether
  6. customThe solvent was removed in vacuo
  7. customto give the crude product as an oil
  8. customPurification by flash chromatography on silica gel eluting with 20% ethyl acetate in hexane

출처 및 근거

ORD 기록
ord-51551e47c08d40f780073ed798d6e6a3
출처 데이터셋
uspto-grants-2004_03
특허 번호
US06699898B2

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