Toluene → HCID 59654356, compound

HRID 2053047Notes

Reaction equation

HRID 2053047 reaction equation
[CH2:1]([O:3][C:4](=[O:12])[C:5]1[CH:10]=[CH:9][CH:8]=[C:7](Br)[CH:6]=1)[CH3:2].C1(C)C=CC=CC=1.[F:20][C:21]([F:33])([F:32])[O:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1B(O)O.C(=O)([O-])[O-].[Na+].[Na+]>C(OCC)(=O)C.O.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(O)C>[CH2:1]([O:3][C:4](=[O:12])[C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=2[O:22][C:21]([F:20])([F:33])[F:32])[CH:6]=1)[CH3:2]

Participants

9

Reactant 4

HCID 1140TolueneHCID 10340Sodium CarbonateHCID 90488Ethyl 3-bromobenzoateHCID 27772042-(Trifluoromethoxy)phenylboronic Acid (contains varying amounts of Anhydride)

Product 1

HCID 59654356HCID 59654356, compound

Reagents, catalysts & solvents 4

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 702EthanolSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 0.94 g (4.58 mmol) of ethyl-3-bromobenzoate in 14.5 Ml of toluene at RT was added 0.25 g (0.218 mmol) of tetrakis(triphenylphosphine) palladium(0), 0.94 g (4.58 mmol) of 2-trifluoromethoxyphenylboronic acid, 2.22 Ml (4.45 mmol) of 2M aqueous sodium carbonate solution and 7 Ml of ethanol. The reaction mixture was heated at reflux for 18 h. The reaction mixture was cooled and diluted with ethyl acetate and water. The organic fraction was separated and washed with saturated NaCl solution (brine), dried over MgSO4, filtered and the filtrate was concentrated to an oil which was purified by chromatography (silica, 1%, 5%, 30% successively ethyl acetate:hexanes) to give the title compound. 1H NMR (CD3OD) (δ, ppm): 8.02 (s, 1H), 7.97 (dd, J=7.8, 1.2 Hz, 1H), 7.60 (dd, J=7.7, 1.3 Hz, 1H), 7.50-7.33 (m, 5H), 4.31(q, 2H), 1.31(t, 3H). Mass Spectrum (ESI) m/e (M+1): 311.2.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 18 h
  3. temperatureThe reaction mixture was cooled
  4. customThe organic fraction was separated
  5. washwashed with saturated NaCl solution (brine)
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationthe filtrate was concentrated to an oil which
  9. customwas purified by chromatography (silica, 1%, 5%, 30% successively ethyl acetate

Sources & evidence

ORD record
ord-cccddf5ba7b544e583e228deb578f612
Source dataset
uspto-grants-2008_02
Patent number
US07326726B2

Reaction notes

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