1,2-Dibromoethane → HCID 67997471、化合物

HRID 1528601ノート

反応式

HRID 1528601 の反応式
[H-].[Na+].[CH2:3]([O:5][C:6](=[O:15])[CH2:7][C:8]1[CH:13]=[C:12]([Br:14])[CH:11]=[CH:10][N:9]=1)[CH3:4].Br[CH2:17][CH2:18]Br>CN(C)C=O>[CH2:3]([O:5][C:6]([C:7]1([C:8]2[CH:13]=[C:12]([Br:14])[CH:11]=[CH:10][N:9]=2)[CH2:18][CH2:17]1)=[O:15])[CH3:4]

参加物

5

反応物 3

HCID 78391,2-DibromoethaneHCID 24758Sodium hydrideHCID 53419398Ethyl 2-(4-broMopyridin-2-yl)acetate

生成物 1

HCID 67997471HCID 67997471、化合物

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

NaH (55% in mineral oil, 0.72 g) was added to a solution of (4-bromo-pyridin-2-yl)-acetic acid ethyl ester (1.80 g) in N,N-dimethylformamide (20 mL) chilled in an ice bath. The resulting mixture was stirred for 10 min at room temperature and then cooled again in an ice bath. 1,2-Dibromoethane (0.70 mL) was added dropwise and the cooling bath was removed. The mixture was stirred at room temperature overnight. Brine was added and the resulting mixture was extracted with ethyl acetate. The combined extracts were washed with brine and dried (MgSO4). The solvent was evaporated and the residue was chromatographed on silica gel (cyclohexane/ethyl acetate 95:5→1:1) to give the title compound as an oil. Yield: 1.28 g (64% of theory); Mass spectrum (ESI+): m/z=270/272 (Br) [M+H]+.

後処理

  1. temperaturechilled in an ice bath
  2. temperaturecooled again in an ice bath
  3. customthe cooling bath was removed
  4. stirringThe mixture was stirred at room temperature overnight
  5. additionBrine was added
  6. extractionthe resulting mixture was extracted with ethyl acetate
  7. washThe combined extracts were washed with brine
  8. dry with materialdried (MgSO4)
  9. customThe solvent was evaporated
  10. customthe residue was chromatographed on silica gel (cyclohexane/ethyl acetate 95:5→1:1)

出典と根拠

ORDレコード
ord-907aa1701e444803b47522d7169a4d53
出典データセット
uspto-grants-2015_07
特許番号
US09090605B2

反応ノート

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