Potassium Carbonate → HCID 86586034, compound

HRID 860540Notes

Reaction equation

HRID 860540 reaction equation
[C:1]12([C:11]3[CH:12]=[C:13](Br)[CH:14]=[CH:15][C:16]=3[O:17][CH2:18][O:19][CH3:20])[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.[CH:22]([C:24]1[CH:29]=[CH:28][C:27](B(O)O)=[CH:26][CH:25]=1)=[O:23].C(=O)([O-])[O-].[K+].[K+]>C1(C)C=CC=CC=1.CCO.O.C(OCC)(=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>[C:1]12([C:11]3[CH:12]=[C:13]([C:27]4[CH:28]=[CH:29][C:24]([CH:22]=[O:23])=[CH:25][CH:26]=4)[CH:14]=[CH:15][C:16]=3[O:17][CH2:18][O:19][CH3:20])[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2

Participants

8

Reactant 3

HCID 11430Potassium CarbonateHCID 5910734-Formylphenylboronic AcidHCID 69583753HCID 69583753, compound

Product 1

HCID 86586034HCID 86586034, compoundYield 78%

Reagents, catalysts & solvents 4

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 8857Ethyl AcetateSolventHCID 21863594Toluene ethanolSolvent

Procedure

A mixture of 3-(1-adamantyl)-4-methoxymethoxy-bromobenzene (8.48 g, 24.16 mmol), 4-formylphenylboronic acid (3.99 g, 26.57 mmol) and potassium carbonate (10.02 g, 72.47 mmol) in 300 mL of toluene:EtOH (4:1) and water (15 mL) was degassed with argon for 30 minutes. Tetrakis(triphenylphosphine)palladium(0) (2.79 g, 2.41 mmol) was added and the mixture heated at reflux for 14 hours. The solution was cooled to room temperature, diluted with ethyl acetate and washed successively with water and brine, dried over anhydrous magnesium sulfate, filtered and evaporated. The residue was purified on silica gel (eluent: hexane:ether, 95:5) to give 7.01 g of 4-[3-(1-adamantyl)-4-methoxymethoxyphenyl]benzaldehyde (78%) as a solid. 1H NMR (300 MHz; CDCl3): δ 1.80 (s, 6H), 2.10–2.17 (m, 9H), 3.55 (s, 3H), 5.29 (s, 2H), 7.20 (d, J=8.4 Hz, 1H), 7.44 (dd, J1=8.7 Hz, J2=2.4 Hz, 1H), 7.52 (d, J=2.4 Hz, 2H), 7.72 (d, J=8.4 Hz, 2H), 7.92 (d, J=7.8 Hz, 2H), 10.03 (s, 1H).

Workup

  1. customwas degassed with argon for 30 minutes
  2. temperaturethe mixture heated
  3. temperatureat reflux for 14 hours
  4. washwashed successively with water and brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue was purified on silica gel (eluent: hexane:ether, 95:5)

Sources & evidence

ORD record
ord-b847388a7fbb40848a9ed23e436b668a
Source dataset
uspto-grants-2006_12
Patent number
US07153875B2

Reaction notes

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