Nitrogen → HCID 1782412, compound

HRID 1464901Notes

Reaction equation

HRID 1464901 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][CH2:10][CH3:11])=[CH:4][CH:3]=1.[CH3:12][O:13][C:14]([C:16]1[CH:21]=[CH:20][C:19](B(O)O)=[CH:18][CH:17]=1)=[O:15].C([O-])([O-])=O.[Na+].[Na+].N#N>C1(C)C=CC=CC=1.CCO.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>[CH2:8]([C:5]1[CH:6]=[CH:7][C:2]([C:19]2[CH:20]=[CH:21][C:16]([C:14]([O:13][CH3:12])=[O:15])=[CH:17][CH:18]=2)=[CH:3][CH:4]=1)[CH2:9][CH2:10][CH3:11]

Participants

7

Reactant 4

HCID 947NitrogenHCID 10340Sodium CarbonateHCID 5210591-Bromo-4-butylbenzeneHCID 27343694-Methoxycarbonylphenylboronic acid

Product 1

HCID 1782412HCID 1782412, compoundYield 86%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 21863594Toluene ethanolSolvent

Procedure

A solution of 1-bromo-4-butylbenzene (100 g, 0.472 mol), 4-(methoxycarbonyl)phenylboronic acid (82.0 g, 0.456 mol), 2 M Na2CO3 (150 g, 1.42 mol) in toluene/EtOH (900 mL/300 mL) was degassed with N2 three times, then Pd(PPh3)4 (27.2 g, 23.6 mmol) was added. The resulting mixture was degassed with N2 three times and then heated to reflux for 5 hrs. After TLC showed the reaction was complete, toluene and EtOH was removed under vacuum. The residue was extracted with EA (30 mL×3). The combined organic layers were washed with brine, dried with Na2SO4. The solvent was removed to give the crude product. The crude product was purified by column chromatography on silica gel eluted with PE, PE:EA (150:1). The solvent was removed to give methyl 4-(4-butylphenyl)benzoate (105 g, yield: 86.0%), as a white solid.

Workup

  1. customThe resulting mixture was degassed with N2 three times
  2. temperatureheated
  3. temperatureto reflux for 5 hrs
  4. customtoluene and EtOH was removed under vacuum
  5. extractionThe residue was extracted with EA (30 mL×3)
  6. washThe combined organic layers were washed with brine
  7. dry with materialdried with Na2SO4
  8. customThe solvent was removed
  9. customto give the crude product
  10. customThe crude product was purified by column chromatography on silica gel
  11. washeluted with PE, PE
  12. customThe solvent was removed

Sources & evidence

ORD record
ord-2547d5a67eee4a36a9d8e1a80a4a5e19
Source dataset
uspto-grants-2015_04
Patent number
US08999922B2

Reaction notes

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