Water → HCID 21021040, compound

HRID 875247Notes

Reaction equation

HRID 875247 reaction equation
[CH:1]([C:3]1[CH:8]=[CH:7][C:6](B(O)O)=[CH:5][CH:4]=1)=[O:2].Br[C:13]1[CH:18]=[CH:17][C:16]([C:19]2[CH:24]=[CH:23][C:22]([O:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])=[CH:21][CH:20]=2)=[CH:15][CH:14]=1.C(=O)([O-])O.[Na+].O>C1COCC1.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>[CH2:26]([O:25][C:22]1[CH:21]=[CH:20][C:19]([C:16]2[CH:17]=[CH:18][C:13]([C:6]3[CH:7]=[CH:8][C:3]([CH:1]=[O:2])=[CH:4][CH:5]=3)=[CH:14][CH:15]=2)=[CH:24][CH:23]=1)[CH2:27][CH2:28][CH2:29][CH3:30]

Participants

7

Reactant 4

HCID 962WaterHCID 516892Sodium BicarbonateHCID 5910734-Formylphenylboronic AcidHCID 28013884-Bromo-4'-(pentyloxy)-1,1'-biphenyl2×

Product 1

HCID 21021040HCID 21021040, compoundYield 58%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

Under an argon atmosphere, (4-formylphenyl)boronic acid (0.54 g, 3.6 mmol), 4-Bromo-4′-pentyloxy-biphenyl (0.958 g, 3 mmol) 1) (A1), sodium hydrogen carbonate (0.76 g, 9 mmol), and tetrakis(triphenylphosphine)palladium (Pd(PPh3)4) (0.057 g, 0.030 mmol) were dissolved in THF (15 mL) and water (15 mL) and stirred under a reflux condition. After they reacted with each other, liquid separation and extraction were performed with water and chloroform. After an organic layer was dried with anhydrous sodium sulfate and filtered, the solvent was distilled off under a reduced pressure. After the obtained reaction mixture was separated and purified with a silica gel column chromatography using chloroform as a moving bed, the mixture was purified by a recrystallization method using chloroform and hexane. Thereby, a white solid of 4″-(pentyloxy)-[1,1′:4′,1″-terphenyl]-4-carbaldehyde (A2) was obtained (0.60 g, yield: 58%). The obtained product (A2) was identified by using a 1H-NMR method. 1H-NMR (CDCl3, 400 MHz) δ=10.06 (s, 1H, CHO), 7.95-7.97 (d, 2H, phenylene), 7.79-7.81 (d, 2H, phenylene), 7.71-7.66 (m, 4H, phenylene), 7.00-6.98 (s, 2H, phenylene), 4.03-3.99 (t, 2H, —O—CH2—), 1.84-1.81 (t, 2H, —CH2—), 1.47-1.40 (m, 4H, —CH2—), and 0.93-0.97 (t, 3H, —CH3). 13C NMR (CDCl3, 100 MHz) δ=191.7, 159.0, 146.7, 141.0, 137.8, 135.2, 132.4, 130.2, 128.0, 127.2, 114.9, 68.1, 29.0, 28.3, 22.7, and 14.1.

Workup

  1. customAfter they reacted with each other,
  2. customliquid separation and extraction
  3. dry with materialAfter an organic layer was dried with anhydrous sodium sulfate
  4. filtrationfiltered
  5. distillationthe solvent was distilled off under a reduced pressure
  6. customAfter the obtained reaction mixture
  7. customwas separated
  8. custompurified with a silica gel column chromatography
  9. customthe mixture was purified by a recrystallization method

Sources & evidence

ORD record
ord-1cfd7ccc8e7c4883a6bd60a60da5005f
Source dataset
uspto-grants-2015_03
Patent number
US08981120B2

Reaction notes

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