Water → Ethyl2-cyano-5-fluorobenzoate

HRID 455290Notes

Reaction equation

HRID 455290 reaction equation
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]

Participants

7

Reactant 4

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

Product 1

HCID 55265172Ethyl2-cyano-5-fluorobenzoate

Reagents, catalysts & solvents 2

HCID 11186Zinc cyanide (Zn(CN)2)CatalystHCID 9811564Bis(dibenzylideneacetone)palladiumCatalyst

Conditions

Temperature
130 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-8885373191a242848b5bc37f044c440d
Source dataset
uspto-grants-2013_07
Patent number
US08497270B2

Reaction notes

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