Phenylboronic Acid → 3,5-Diphenyl-4-[(2-methoxyethoxy)methoxy]-benzaldehyde

HRID 324111

Reaction equation

HRID 324111 reaction equation
I[C:2]1[CH:3]=[C:4]([CH:7]=[C:8](I)[C:9]=1[O:10][CH2:11][O:12][CH2:13][CH2:14][O:15][CH3:16])[CH:5]=[O:6].[C:18]1(B(O)O)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>COCCOC.O.CC([O-])=O.CC([O-])=O.[Pd+2]>[C:18]1([C:2]2[CH:3]=[C:4]([CH:7]=[C:8]([C:2]3[CH:3]=[CH:4][CH:7]=[CH:8][CH:9]=3)[C:9]=2[O:10][CH2:11][O:12][CH2:13][CH2:14][O:15][CH3:16])[CH:5]=[O:6])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

6

Reactant 2

HCID 66827Phenylboronic AcidHCID 222376563,5-Diiodo-4-(2-methoxyethoxymethoxy)benzaldehyde

Product 1

HCID 222375093,5-Diphenyl-4-[(2-methoxyethoxy)methoxy]-benzaldehydeYield 155.5%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

A mixture of 3,5-diiodo-4-(2-methoxyethoxymethyloxy)-benzaldehyde (19.094 g, 41.327 mmol), Pd(OAc)2(0.185 g, 0.02 mmol), phenylboronic acid (11.429 g, 90.920 mmol) and Ba(OH)2-8H2O (39.114 g, 123.981 mmol) in DME (700 ml) and water (110 ml) was refluxed. After 90 minutes, the reaction mixture was cooled, concentrated to about 400 ml and the residue extracted with EtOAc (1×300 ml, 3×100 ml). The combined organics were washed with saturated NaHCO3 (3×75 ml), water (2×75 ml), brine (2×75 ml), dried over Na2SO4, filtered and the filtrate concentrated in vac and dried. The residue was purified by flash chromatography (hexane, 5% and 12% EtOAc/Hex) to give the product as a light yellow viscous oil (11.645 g, 78%); 1H NMR (400 MHz, DMSO-d6) δ2.79-2.82 (m, 2H), 2.89-2.92 (m, 2H), 3.02 (s, 3H), 4.42 (s, 2H), 7.42-7.46 (m, 2H), 7.48-7.54 (m, 4H), 7.62-7.66 (m, 4H), 7.91 (s, 2H), 10.07 (s, 1H); IR (film) 3050, 2880, 1690,1580 cm−1; mass spectrum [EI], m/z 362 M+.

Workup

  1. temperaturewas refluxed
  2. temperaturethe reaction mixture was cooled
  3. concentrationconcentrated to about 400 ml
  4. extractionthe residue extracted with EtOAc (1×300 ml, 3×100 ml)
  5. washThe combined organics were washed with saturated NaHCO3 (3×75 ml), water (2×75 ml), brine (2×75 ml)
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationthe filtrate concentrated in vac
  9. customdried
  10. customThe residue was purified by flash chromatography (hexane, 5% and 12% EtOAc/Hex)

Sources & evidence

ORD record
ord-2eeec29e2f884b189580f813d2b7e05a
Source dataset
uspto-grants-2001_04
Patent number
US06214877B1

Linked notes

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