Ethyl chloroformate → Ethyl 3,5-dibromoisonicotinate

HRID 1501277ノート

反応式

HRID 1501277 の反応式
[Br:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([Br:8])[CH:7]=1.[Li+].CC([N-]C(C)C)C.[C:17](Cl)(=[O:21])[O:18][CH2:19][CH3:20]>C1COCC1>[Br:8][C:6]1[CH:5]=[N:4][CH:3]=[C:2]([Br:1])[C:7]=1[C:17]([O:18][CH2:19][CH3:20])=[O:21]

参加物

5

反応物 3

HCID 10928Ethyl chloroformateHCID 693693,5-DibromopyridineHCID 2724682Lithium diisopropylamide

生成物 1

HCID 46311332Ethyl 3,5-dibromoisonicotinate収率 29%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-78 °C

実験手順

To a solution of 3,5-dibromopyridine (5 g, 21.11 mmol) in THF was added LDA (2 M in THF, 12.66 ml, 25.33 mmol) at −78° C. The mixture was stirred at −78° C. for 45 min. Then ethyl carbonochloridate (2.29 g, 21.11 mmol) was added and the mixture stirred at −78° C. for 1 hours. After reaction completed, the reaction was quenched by addition of 5 mL of saturated NH4Cl and extracted with EtOAc. The extractions were combined, washed with H2O, dried over Na2SO4 and concentrated under vacuum. The residue was purified by flash column (Eluent: PE/EtOAc=10:1), to give ethyl 3,5-dibromoisonicotinate as a yellow solid. (1.9 g, yield 29%) LCMS (M+H+) m/z: calcd 306.8. found 309.7.

後処理

  1. stirringthe mixture stirred at −78° C. for 1 hours
  2. customAfter reaction
  3. customthe reaction was quenched by addition of 5 mL of saturated NH4Cl
  4. extractionextracted with EtOAc
  5. extractionThe extractions
  6. washwashed with H2O
  7. dry with materialdried over Na2SO4
  8. concentrationconcentrated under vacuum
  9. customThe residue was purified by flash column (Eluent: PE/EtOAc=10:1)

出典と根拠

ORDレコード
ord-e5995e6bb43b4cb283d58ea989579d1c
出典データセット
uspto-grants-2015_12
特許番号
US09206128B2

反応ノート

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