Triphenylphosphine → HCID 68699250, compound

HRID 2244321Notes

Reaction equation

HRID 2244321 reaction equation
[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[CH:8][C:7](Br)=[CH:6][C:5]=1[Cl:11].[CH:13]1(B(O)O)[CH2:15][CH2:14]1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1(C)C=CC=CC=1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O>[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[CH:8][C:7]([CH:13]2[CH2:15][CH2:14]2)=[CH:6][C:5]=1[Cl:11]

Participants

8

Reactant 4

HCID 11776TriphenylphosphineHCID 62657Potassium Phosphate, TribasicHCID 2760897Cyclopropylboronic acidHCID 22058730Methyl 4-Bromo-2-chlorobenzoate

Product 1

HCID 68699250HCID 68699250, compound

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolvent2×HCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

2.1 g of crude 4-bromo-2-chloro-benzoic acid methyl ester (8.42 mmol) were dissolved in 38 ml toluene and treated with 0.94 g of cyclopropylboronic acid (10.94 mmol), 6.25 g of potassium phosphate (29.46 mmol), 236 mg of triphenylphosphine (0.84 mmol), 94 mg of palladium acetate (0.42 mmol) and 1.9 ml water. The reaction mixture was stirred 17 h at 100° C. under Argon. After cooling down to RT, the reaction mixture was treated with 80 ml water, extracted with 2×80 ml EtOAc, washed with brine, dried over magnesium sulfate, filtered and concentrated in vacuo. The remaining residue was purified by silicagel chromatography (100 g silicagel, heptane/AcOEt 95:5) leading to 1.17 g of 2-chloro-4-cyclopropyl-benzoic acid methyl ester (66%) as a yellow oil. MS (+cEI): 210.1 (M).

Workup

  1. temperatureAfter cooling down to RT
  2. extractionextracted with 2×80 ml EtOAc
  3. washwashed with brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe remaining residue was purified by silicagel chromatography (100 g silicagel, heptane/AcOEt 95:5)

Sources & evidence

ORD record
ord-516fb4d532204b009e34a4d629828514
Source dataset
uspto-grants-2010_03
Patent number
US07678818B2

Reaction notes

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