Ethyl Acetate → 1035689-60-1

HRID 2382170Notes

Reaction equation

HRID 2382170 reaction equation
Br[C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[C:4]([F:9])[CH:3]=1.C([O-])([O-])=O.[K+].[K+].[CH2:16]([O:18][C:19]1[CH:20]=[C:21](B(O)O)[CH:22]=[CH:23][CH:24]=1)[CH3:17].C(OCC)(=O)C>C1(C)C=CC=CC=1.CO.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH2:16]([O:18][C:19]1[CH:24]=[C:23]([C:2]2[CH:8]=[CH:7][C:5]([NH2:6])=[C:4]([F:9])[CH:3]=2)[CH:22]=[CH:21][CH:20]=1)[CH3:17]

Participants

8

Reactant 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 1230504-Bromo-2-fluoroanilineHCID 27739203-Ethoxybenzeneboronic acid

Product 1

HCID 669973551035689-60-1Yield 95.9%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 887MethanolSolventHCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 4-bromo-2-fluoroaniline (3.2 g, 17.05 mmol), 2M K2CO3 (24 ml, 48.00 mmol), Pd(PPh3)4 (1.2 g, 1.02 mmol) in toluene (120 ml) under nitrogen atmosphere was added dropwise a solution of the 3-ethoxyphenylboronic acid (4.25 g, 25.61 mmol) in 31 ml of MeOH. The mixture was heated to 80° C. overnight and then cooled to room temperature. Ethyl acetate was added and washed twice with a K2CO3 aqueous solution. The organic layer was washed with brine, dried over magnesium sulphate, filtered and the solvent evaporated under vacuum. The residue obtained was purified by flash chromatography eluting with Hexane/AcOEt (from 10/1 to 8/1). The solid obtained was recrystallized in hexane to yield 3.78 g of the desired compound as a white solid. Yield=72%

Workup

  1. temperaturecooled to room temperature
  2. washwashed twice with a K2CO3 aqueous solution
  3. washThe organic layer was washed with brine
  4. dry with materialdried over magnesium sulphate
  5. filtrationfiltered
  6. customthe solvent evaporated under vacuum
  7. customThe residue obtained
  8. customwas purified by flash chromatography
  9. washeluting with Hexane/AcOEt (from 10/1 to 8/1)
  10. customThe solid obtained
  11. customwas recrystallized in hexane

Sources & evidence

ORD record
ord-8a9e1fb6c9e7424885ef3a95956534e4
Source dataset
uspto-grants-2012_09
Patent number
US08258308B2

Reaction notes

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