Cyclopropylboronic acid → (5-Cyclopropyl-2,4-dimethyl-phenyl)-acetic acid methyl ester

HRID 1022379Notes

Reaction equation

HRID 1022379 reaction equation
[CH3:1][O:2][C:3](=[O:14])[CH2:4][C:5]1[CH:10]=[C:9](Br)[C:8]([CH3:12])=[CH:7][C:6]=1[CH3:13].[CH:15]1(B(O)O)[CH2:17][CH2:16]1>C1(C)C=CC=CC=1.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>[CH3:1][O:2][C:3](=[O:14])[CH2:4][C:5]1[CH:10]=[C:9]([CH:15]2[CH2:17][CH2:16]2)[C:8]([CH3:12])=[CH:7][C:6]=1[CH3:13]

Participants

5

Reactant 2

HCID 2760897Cyclopropylboronic acidHCID 22648849(5-Bromo-2,4-dimethyl-phenyl)-acetic acid methyl ester

Product 1

HCID 59614579(5-Cyclopropyl-2,4-dimethyl-phenyl)-acetic acid methyl esterYield 49.1%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Procedure

To a solution of 6.0 g of (5-bromo-2,4-dimethyl-phenyl)-acetic acid methyl ester (WO99/48869) in 100 ml of toluene is added 2.2 g of cyclopropylboronic acid and 20 g of potassium phosphate tribasic trihydrate at room temperature. The reaction mixture is stirred for 5 minutes under nitrogen atmosphere, followed by further addition of 1.2 g of tetrakis(triphenylphosphine)palladium(0). After heating and stirring for 16 hours at 110° C., the reaction mixture is filtered, the solvent removed in vacuo and the residue is subjected to silica gel chromatography (isohexane/diethyl ether 2:1) to yield 2.5 g of (5-cyclopropyl-2,4-dimethyl-phenyl)-acetic acid methyl ester.

Workup

  1. temperatureAfter heating
  2. stirringstirring for 16 hours at 110° C.
  3. filtrationthe reaction mixture is filtered
  4. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-d538f88fe706490b9895308da3927297
Source dataset
uspto-grants-2014_05
Patent number
US08722578B2

Reaction notes

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