Water → N,N-Diethyl-2-(trifluoromethoxy)-4-vinylbenzamide

HRID 1159058Notes

Reaction equation

HRID 1159058 reaction equation
[CH2:1]([N:3]([CH2:18][CH3:19])[C:4](=[O:17])[C:5]1[CH:10]=[CH:9][C:8](Br)=[CH:7][C:6]=1[O:12][C:13]([F:16])([F:15])[F:14])[CH3:2].C(=O)([O-])[O-].[K+].[K+].B1(C=C)OB([CH:32]=[CH2:33])OB(C=C)O1.C1C=CN=CC=1.O>C1COCC1.[Cl-].[Na+].O.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>[CH2:1]([N:3]([CH2:18][CH3:19])[C:4](=[O:17])[C:5]1[CH:10]=[CH:9][C:8]([CH:32]=[CH2:33])=[CH:7][C:6]=1[O:12][C:13]([F:16])([F:15])[F:14])[CH3:2]

Participants

8

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 27348062,4,6-Trivinylboroxin-Pyridine ComplexHCID 686878354-bromo-N,N-diethyl-2-(trifluoromethoxy)benzamide

Product 1

HCID 68691199N,N-Diethyl-2-(trifluoromethoxy)-4-vinylbenzamideYield 88.7%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 8028TetrahydrofuranSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To a stirring degassed solution of N,N-diethyl-4-bromo-2-(trifluoromethoxy)benzamide (2373 mg, 7 mmol) in THF (40 mL) was added tetrakis(triphenylphosphine)palladium(0) (97 mg, 0.08 mmol). After 15 min., potassium carbonate (2898 mg, 21 mmol), 2,4,6-trivinylcyclotriboroxane pyridine complex (2663 mg, 7 mmol), and water (8 mL). The reaction was heated to reflux for 3 h and then cooled to room temperature. The reaction was diluted with brine and extracted with EtOAc (3×25 mL). The organic layers were combined, dried over Na2SO4, and conc. in vacuo to a pale yellow oil. The oil was purified by flash chromatography (SiO2, 0-50% EtOAc in hexanes) to give 1783 mg of the desired product as a colorless oil. MS (ESI) 288 (M+H).

Workup

  1. temperatureThe reaction was heated
  2. temperatureto reflux for 3 h
  3. extractionextracted with EtOAc (3×25 mL)
  4. dry with materialdried over Na2SO4
  5. customThe oil was purified by flash chromatography (SiO2, 0-50% EtOAc in hexanes)

Sources & evidence

ORD record
ord-6ea44087dae241869a0934fc829c40d0
Source dataset
uspto-grants-2010_10
Patent number
US07812024B2

Reaction notes

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