Ethyl Acetate → HCID 59553713, compound

HRID 1170937Notes

Reaction equation

HRID 1170937 reaction equation
[F:1][C:2]([F:14])([F:13])[O:3][C:4]1[CH:5]=[C:6](B(O)O)[CH:7]=[CH:8][CH:9]=1.[O-]P([O-])([O-])=O.[K+].[K+].[K+].O.[F:24][C:25]([F:38])([F:37])[C:26]1[CH:31]=[CH:30][C:29]([CH2:32][CH2:33][C:34](Cl)=[O:35])=[CH:28][CH:27]=1.C(OCC)(=O)C>C1(C)C=CC=CC=1>[F:1][C:2]([F:14])([F:13])[O:3][C:4]1[CH:5]=[C:6]([C:34](=[O:35])[CH2:33][CH2:32][C:29]2[CH:28]=[CH:27][C:26]([C:25]([F:37])([F:38])[F:24])=[CH:31][CH:30]=2)[CH:7]=[CH:8][CH:9]=1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 27343853-(Trifluoromethoxy)phenylboronic Acid (contains varying amounts of Anhydride)HCID 10331694HCID 10331694, compoundHCID 22031701Potassium phosphate, tribasic, monohydrate

Product 1

HCID 59553713HCID 59553713, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
110 °C

Procedure

To a solution of 522 mg (2.5 mmol) 3-(trifluoromethoxy)phenylboronic acid in 10 ml toluene under argon at RT, was added successively 29.7 mg (0.04 mmol) Pd(PPh3)2Cl, 776.5 mg (3.2 mmol) K3PO4.H2O and 500 mg (2.1 mmol) 3-(4-Trifluoromethyl-phenyl)-propionyl chloride (CAS: 539855-79-3). The reaction mixture was heated at 110° C. for 3 h, cooled to RT and ethyl acetate was added. The solution was washed successively with NaHCO3 sat., water and brine. The organic phase was dried over Na2SO4 and evaporated. The crude oil was purified with flash column chromatography on silica eluting with a gradient formed from heptane and ethylacetate to provide 0.44 g (58%) of the title compound as colorless oil. MS (m/e): 363.0 (MH+).

Workup

  1. temperaturecooled to RT
  2. washThe solution was washed successively with NaHCO3 sat., water and brine
  3. dry with materialThe organic phase was dried over Na2SO4
  4. customevaporated
  5. customThe crude oil was purified with flash column chromatography on silica eluting with a gradient
  6. customformed from heptane and ethylacetate

Sources & evidence

ORD record
ord-9001d2bf93a3423a918473630e9e1240
Source dataset
uspto-grants-2010_11
Patent number
US07829563B2

Reaction notes

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