Sodium Carbonate → 4'-Methoxy-3-methyl-1,1'-biphenyl-4-carbonitrile

HRID 1167848

Reaction equation

HRID 1167848 reaction equation
Br[C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[C:4]([CH3:10])[CH:3]=1.C([O-])([O-])=O.[Na+].[Na+].[CH3:17][O:18][C:19]1[CH:24]=[CH:23][C:22](B(O)O)=[CH:21][CH:20]=1>C1C=CC=CC=1.C(O)C.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>[CH3:17][O:18][C:19]1[CH:24]=[CH:23][C:22]([C:2]2[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[C:4]([CH3:10])[CH:3]=2)=[CH:21][CH:20]=1

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 1442674-Bromo-2-methylbenzonitrileHCID 201262(4-Methoxyphenyl)boronic acid

Product 1

HCID 112183464'-Methoxy-3-methyl-1,1'-biphenyl-4-carbonitrileYield 102.7%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 241BenzeneSolventHCID 702EthanolSolvent

Conditions

Temperature
75 °C

Procedure

4-Bromo-2-methylbenzonitrile (4.9 g, 25.0 mmol), Pd(PPh3)4 (578 mg) in benzene (50 mL) and 2.0 M aqueous solution of Na2CO3 (25 mL, 50.0 mmol) was treated with 4-methoxyphenylboronic acid (4.56 g, 30.0 mmol) in ethanol (20 mL) and heated at 75° C. for 17 hours. The mixture was allowed to cool to room temperature and the phases were separated. The aqueous phase was extracted with diethyl ether (3×40 mL). The original benzene layer and the diethyl ether extracts were combined, filtered over celite, dried over sodium sulfate, and filtered. The filtrate was concentrated under reduced pressure and the residue was purified by chromatography over silica using a mixture of hexane/CH2Cl2 (3:1) to provide the title compound as a white powder (5.73 g, 85% yield). 1HNMR (300 MHz, CDCl3) δ2.35 (3H), 3.70 (s, 3H), 6.80-7.50 (m, 7H); MS (DCI) m/z 224 (M+H)+.

Workup

  1. temperatureto cool to room temperature
  2. customthe phases were separated
  3. extractionThe aqueous phase was extracted with diethyl ether (3×40 mL)
  4. filtrationfiltered over celite
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated under reduced pressure
  8. customthe residue was purified by chromatography over silica using
  9. additiona mixture of hexane/CH2Cl2 (3:1)

Sources & evidence

ORD record
ord-5fb72cccb0dc49bca108d433dbeda2d6
Source dataset
uspto-grants-2003_09
Patent number
US06620839B2

Linked notes

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