3-Nitrophenylboronic Acid → HCID 57143370, compound

HRID 983792Notes

Reaction equation

HRID 983792 reaction equation
[CH3:1][O:2][C:3](=[O:15])[C:4]1[CH:9]=[C:8]([Cl:10])[C:7](C)=[C:6](I)[C:5]=1[O:13][CH3:14].[N+:16]([C:19]1[CH:20]=[C:21](B(O)O)[CH:22]=[CH:23][CH:24]=1)([O-:18])=[O:17].C([O-])([O-])=O.[K+].[K+]>C1(C)C=CC=CC=1.C(O)C.CCOCC>[CH3:1][O:2][C:3]([C:4]1[C:5]([O:13][CH3:14])=[C:6]([C:23]2[CH:22]=[CH:21][CH:20]=[C:19]([N+:16]([O-:18])=[O:17])[CH:24]=2)[CH:7]=[C:8]([Cl:10])[CH:9]=1)=[O:15]

Participants

7

Reactant 3

HCID 16773-Nitrophenylboronic AcidHCID 11430Potassium CarbonateHCID 86759611HCID 86759611, compound

Product 1

HCID 57143370HCID 57143370, compound

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 1140TolueneSolventHCID 3283Diethyl EtherSolvent

Procedure

To a solution of methyl,5-chloro-3-iodo-2-methoxybenzoic acid methyl ester (0.80 g, 2.5 mmol) and tetrakis (triphenylphosphine)palladium(0) (0.085 g, 0.074 mmol) in toluene (12 mL) was added 3-nitrobenzene-boronic acid (0.45 g, 2.7 mmol) dissolved in 1 mL of ethanol. Aqueous 2 N K2CO3 (2.7 mL, 5.4 mmol) was added and the mixture was heated to reflux for 18 h. The mixture was diluted with ether, washed with 3:1 saturated NaHCO3/conc. ammonium hydroxide, 0.1 M EDTA, saturated NaCl, and dried (Na2SO4). The solvent was removed under reduced pressure, and the crude material was purified by silica gel chromatography employing a gradient elution of 60 to 75% CH2Cl2/hexane. 5-Chloro-2-methoxy-3′-nitro-biphenyl-3-carboxylic acid methyl ester 43 was obtained as an amber waxy solid (0.59 g, 75% yield).

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 18 h
  3. washwashed with 3:1 saturated NaHCO3/conc
  4. dry with materialammonium hydroxide, 0.1 M EDTA, saturated NaCl, and dried (Na2SO4)
  5. customThe solvent was removed under reduced pressure
  6. customthe crude material was purified by silica gel chromatography
  7. washa gradient elution of 60 to 75% CH2Cl2/hexane

Sources & evidence

ORD record
ord-eeb55e735fbe423eac9eda4d1a92e2ab
Source dataset
uspto-grants-2005_03
Patent number
US06867200B1

Reaction notes

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