Water → Ethyl2-cyano-5-fluorobenzoate

HRID 455290노트

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HRID 455290 반응식
Br[C:2]1[CH:12]=[CH:11][C:10]([F:13])=[CH:9][C:3]=1[C:4]([O:6][CH2:7][CH3:8])=[O:5].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O.[CH3:34][N:35](C=O)C>[C-]#N.[Zn+2].[C-]#N.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[C:34]([C:2]1[CH:12]=[CH:11][C:10]([F:13])=[CH:9][C:3]=1[C:4]([O:6][CH2:7][CH3:8])=[O:5])#[N:35]

참가 물질

7

반응물 4

HCID 962WaterHCID 6228DimethylformamideHCID 11776TriphenylphosphineHCID 15037299Ethyl 2-bromo-5-fluorobenzoate

생성물 1

HCID 55265172Ethyl2-cyano-5-fluorobenzoate

시약·촉매·용매 2

HCID 11186Zinc cyanide (Zn(CN)2)촉매HCID 9811564Bis(dibenzylideneacetone)palladium촉매

반응 조건

온도
130 °C

실험 절차

Zinc cyanide (26.5 g; 0.225 mol) and Pd2(dba)3 (1.9 g; 3.4 mmol) were added to a solution of ethyl 2-bromo-5-fluorobenzoate (27.9 g; 0.112 mol) in DMF (71 ml). Triphenyl phosphine (2.9 g; 11 mmol) was added and then the reaction mixture was stirred at 130° C. under nitrogen atmosphere for 4 hours. The mixture was poured out into H2O (300 ml) and then extracted with EtOAc (200 ml). The organic layer was separated, washed with H2O (2×100 ml), brine (100 ml), dried (MgSO4), filtered and the solvent was evaporated.

후처리

  1. extractionextracted with EtOAc (200 ml)
  2. customThe organic layer was separated
  3. washwashed with H2O (2×100 ml), brine (100 ml)
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customthe solvent was evaporated

출처 및 근거

ORD 기록
ord-8885373191a242848b5bc37f044c440d
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08497270B2

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