Ethyl difluoroacetate → HCID 86638499, 화합물

HRID 216344노트

반응식

HRID 216344 반응식
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

참가 물질

5

반응물 3

HCID 9961Ethyl difluoroacetateHCID 693532,5-DibromopyridineHCID 178418339Butyllithium

생성물 1

HCID 86638499HCID 86638499, 화합물수율 56.5%

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-bb5e77370f144043b51db303a0569305
출처 데이터셋
uspto-grants-2012_06
특허 번호
US08193228B2

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