Ethyl difluoroacetate → HCID 86638499、化合物

HRID 216344ノート

反応式

HRID 216344 の反応式
Br[C:2]1[CH:7]=[CH:6][C:5]([Br:8])=[CH:4][N:3]=1.[Li]CCCC.[F:14][CH:15]([F:21])[C:16](OCC)=[O:17]>C1(C)C=CC=CC=1>[Br:8][C:5]1[CH:6]=[CH:7][C:2]([C:16](=[O:17])[CH:15]([F:21])[F:14])=[N:3][CH:4]=1

参加物

5

反応物 3

HCID 9961Ethyl difluoroacetateHCID 693532,5-DibromopyridineHCID 178418339Butyllithium

生成物 1

HCID 86638499HCID 86638499、化合物収率 56.5%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

To a solution of 2,5-dibromopyridine (15.21 g, 64 mmol) in anhydrous toluene (150 mL) at −78° C. under nitrogen was added dropwise with n-BuLi (2.5 M in hexane, 25 mL, 62 mmol). Stirring was continued at −78° C. for 2 h, then ethyl difluoroacetate (11 g, 80 mmol) was added dropwise at −78° C. The mixture was stirred overnight while the temperature rose to room temperature. The mixture was partitioned between EtOAc and brine, the water layer was extracted with EtOAc, the combined organic extracts were dried and concentrated, flash chromatography on silica gel afforded 8.53 g of 1-(5-bromopyridin-2-yl)-2,2-difluoroethanone as white solid.

後処理

  1. stirringThe mixture was stirred overnight while the temperature
  2. customrose to room temperature
  3. customThe mixture was partitioned between EtOAc and brine
  4. extractionthe water layer was extracted with EtOAc
  5. customthe combined organic extracts were dried
  6. concentrationconcentrated

出典と根拠

ORDレコード
ord-bb5e77370f144043b51db303a0569305
出典データセット
uspto-grants-2012_06
特許番号
US08193228B2

反応ノート

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