1-Bromo-2-nitrobenzene → HCID 10966276, compound

HRID 2306240Notes

Reaction equation

HRID 2306240 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5](B(O)O)[CH:6]=[CH:7][CH:8]=1.Br[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[N+:19]([O-:21])=[O:20].C([O-])([O-])=O.[K+].[K+]>O.COCCOC.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]1[CH:4]=[C:5]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[N+:19]([O-:21])=[O:20])[CH:6]=[CH:7][CH:8]=1

Participants

7

Reactant 3

HCID 113411-Bromo-2-nitrobenzeneHCID 11430Potassium CarbonateHCID 2734370(3-Methoxyphenyl)boronic acid

Product 1

HCID 10966276HCID 10966276, compound

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolvent2×HCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
110 °C

Procedure

3-Methoxyphenyl boronic acid (7.4 g, 48.71 mmol), 1-bromonitrobenzene (10.25 g, 40.59 mmol) and K2CO3 (28.05 g, 202.9 mmol) were dissolved in H2O (85 mL) and ethylene glycol dimethyl ether (170 mL). The solution was degassed, Pd(PPh3)4 (1.7 g, 1.50 mmol) was added and the vessel was heated to 110° C. under argon for 5 hours. The reaction was cooled, diluted with water and extracted with EtOAc (3×). The combined organic extracts were dried over Na2SO4, filtered and concentrated in vacuo. The residue was crystallized from EtOAc/Hex. The mother liquor was concentrated in vacuo and chromatographed on silica gel, eluting with a gradient of 1 to 10% EtOAc in hexanes, to yield the above-titled compound.

Workup

  1. customThe solution was degassed
  2. temperatureThe reaction was cooled
  3. extractionextracted with EtOAc (3×)
  4. dry with materialThe combined organic extracts were dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was crystallized from EtOAc/Hex
  8. concentrationThe mother liquor was concentrated in vacuo
  9. customchromatographed on silica gel
  10. washeluting with a gradient of 1 to 10% EtOAc in hexanes

Sources & evidence

ORD record
ord-9eb4d4716ccc40bbb765ab9ecbebb338
Source dataset
uspto-grants-2002_08
Patent number
US06441017B1

Reaction notes

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