(2,6-Diethylphenyl)boronic acid → HCID 18437821, compound

HRID 457401Notes

Reaction equation

HRID 457401 reaction equation
Br[C:2]1[N:6]([Cl:7])[C:5]([Cl:8])=[C:4]([CH:9]([O:11][CH3:12])[CH3:10])[N:3]=1.[CH2:13]([C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([CH2:21][CH3:22])[C:16]=1B(O)O)[CH3:14]>C1(C)C=CC=CC=1.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>[CH2:13]([C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([CH2:21][CH3:22])[C:16]=1[C:2]1[N:6]([Cl:7])[C:5]([Cl:8])=[C:4]([CH:9]([O:11][CH3:12])[CH3:10])[N:3]=1)[CH3:14]

Participants

5

Reactant 2

HCID 18437832(2,6-Diethylphenyl)boronic acidHCID 18437837HCID 18437837, compound

Product 1

HCID 18437821HCID 18437821, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Conditions

Temperature
110 °C

Procedure

A solution containing 2-bromo-1-methoxyethyl-3,4-dichloroimidazole (2.74 g, 10 mmol), 2,6-diethylphenylboronic acid (2.14 g, 12 mmol.) and Pd(PPh3)4 (0.23 mg, 0.2 mmol) in toluene/2M Na2CO3 (30 ml/15 mL) in a sealed tube is degassed, then allowed to heat to 110° C. overnight. The organic layer is separated and concentrated in vacuo to dryness. The residue is purified by column chromatography on silica gel (hexane/ethyl acetate 100/5) to obtain the 2-(2,6-diethylphenyl)-1-methoxyethyl-3,4-dichloroimidazole. Synthesis of 2-(2,6-diethylphenyl)-1-methoxyethyl-4-chloro-imidazole-3-carboxaldehyde

Workup

  1. customis degassed
  2. customThe organic layer is separated
  3. concentrationconcentrated in vacuo to dryness
  4. customThe residue is purified by column chromatography on silica gel (hexane/ethyl acetate 100/5)

Sources & evidence

ORD record
ord-938dfd8e03c24e4386b175b055a5bb93
Source dataset
uspto-grants-2007_03
Patent number
US07186734B2

Reaction notes

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