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

HRID 48044ノート

反応式

HRID 48044 の反応式
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]

参加物

7

反応物 4

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

生成物 1

HCID 37100393-(Pyridin-2-yl)benzaldehyde収率 38.2%

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
-78 °C

実験手順

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+].

後処理

  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

出典と根拠

ORDレコード
ord-51551e47c08d40f780073ed798d6e6a3
出典データセット
uspto-grants-2004_03
特許番号
US06699898B2

反応ノート

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