Sodium Carbonate → Methyl 4,5-dicyclopropyl-2-isopropoxybenzoate

HRID 2272475Notes

Reaction equation

HRID 2272475 reaction equation
[CH:1]1(B(O)O)[CH2:3][CH2:2]1.C(=O)([O-])[O-].[Na+].[Na+].C1(P(C2CCCCC2)C2C=CC=CC=2C2C(OC)=CC=CC=2OC)CCCCC1.Br[C:43]1[C:44]([CH:57]2[CH2:59][CH2:58]2)=[CH:45][C:46]([O:53][CH:54]([CH3:56])[CH3:55])=[C:47]([CH:52]=1)[C:48]([O:50][CH3:51])=[O:49]>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].O.C1(C)C=CC=CC=1>[CH:57]1([C:44]2[C:43]([CH:1]3[CH2:3][CH2:2]3)=[CH:52][C:47]([C:48]([O:50][CH3:51])=[O:49])=[C:46]([O:53][CH:54]([CH3:56])[CH3:55])[CH:45]=2)[CH2:59][CH2:58]1

Participants

8

Reactant 4

HCID 10340Sodium CarbonateHCID 2760897Cyclopropylboronic acidHCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenylHCID 90423660Methyl 5-bromo-4-cyclopropyl-2-isopropoxybenzoate

Product 1

HCID 90423073Methyl 4,5-dicyclopropyl-2-isopropoxybenzoateYield 97.8%

Reagents, catalysts & solvents 3

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

Cyclopropylboronic acid (2.83 g), a 2 M aqueous sodium carbonate solution (33 mL), tris(dibenzylideneacetone)dipalladium(0) (1.41 g), and dicyclohexyl(2′,6′-dimethoxybiphenyl-2-yl)phosphine (1.36 g) were added at room temperature to a toluene (100 mL) solution of methyl 5-bromo-4-cyclopropyl-2-isopropoxybenzoate (6.89 g), and the mixture was stirred at 100 C for 15 hours in an argon atmosphere. Water was added to the reaction mixture at room temperature. The mixture was filtered through celite, and then, the filtrate was subjected to extraction with ethyl acetate. The obtained organic layer was washed with water and saturated saline in this order and dried over anhydrous magnesium sulfate, and then, the solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate) to obtain the title compound (5.90 g)

Workup

  1. filtrationThe mixture was filtered through celite
  2. extractionthe filtrate was subjected to extraction with ethyl acetate
  3. washThe obtained organic layer was washed with water and saturated saline in this order
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationthe solvent was distilled off under reduced pressure
  6. customThe obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-1800e9ef298c4d96b549eace14b10749
Source dataset
uspto-grants-2015_09
Patent number
US09120777B2

Reaction notes

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