Potassium Phosphate, Tribasic → HCID 70917093, compound

HRID 338881Notes

Reaction equation

HRID 338881 reaction equation
Br[C:2]1[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].P([CH:27]1[CH2:32][CH2:31]CCC1)(C1CCCCC1)C1CCCCC1.[O-]P([O-])([O-])=O.[K+].[K+].[K+].C1(B(O)O)CC1>C1(C)C=CC=CC=1.O.CC([O-])=O.CC([O-])=O.[Pd+2].C(OCC)(=O)C>[CH:31]1([C:2]2[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][CH:8]=[CH:7][C:3]=2[C:4]([OH:6])=[O:5])[CH2:32][CH2:27]1

Participants

9

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 684522-Bromo-3-nitrobenzoic acidHCID 75806TricyclohexylphosphineHCID 2760897Cyclopropylboronic acid

Product 1

HCID 70917093HCID 70917093, compoundYield 645.6%

Reagents, catalysts & solvents 4

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolvent2×HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 2-bromo-3-nitrobenzoic acid (1.17 g, 4.28 mmol), Pd(OAc)2 (0.048 g, 0.21 mmol), P(Cy)3 (0.132 g, 0.471 mmol), K3PO4 (3.18 g, 15.0 mmol) and cyclopropylboronic acid (0.735 g, 8.56 mmol) in toluene (4 mL) and water (1 mL) was stirred at 100° C. for 6 hours. After cooling to ambient temperature, ethyl acetate (20 mL) and water (5 mL) were added. The aqueous layer was separated and acidified with saturated potassium hydrogen sulfate to about pH 3-4. The resulting solid was collected by filtration to give 2-cyclopropyl-3-nitrobenzoic acid (0.63 g, 71.0%) as a solid.

Workup

  1. customThe aqueous layer was separated
  2. filtrationThe resulting solid was collected by filtration

Sources & evidence

ORD record
ord-88b218a09866498a935a6d99980da064
Source dataset
uspto-grants-2014_11
Patent number
US08889704B2

Reaction notes

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