Sodium Carbonate → HCID 59229504, compound

HRID 1640097

Reaction equation

HRID 1640097 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[N+:10]([O-:12])=[O:11])[CH2:5]Cl.[F:13][C:14]([F:29])([F:28])[C:15]1[CH:16]=[C:17](B(O)O)[CH:18]=[C:19]([C:21]([F:24])([F:23])[F:22])[CH:20]=1.C(=O)([O-])[O-].[Na+].[Na+]>O.COCCOC.C(OCC)(=O)C>[F:13][C:14]([F:28])([F:29])[C:15]1[CH:16]=[C:17]([CH:18]=[C:19]([C:21]([F:22])([F:23])[F:24])[CH:20]=1)[CH2:5][C:4]1[CH:7]=[CH:8][C:9]([N+:10]([O-:12])=[O:11])=[C:2]([CH3:1])[CH:3]=1

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 87687Alpha-chloro-3-methyl-4-nitrotolueneHCID 1562653,5-Bis-trifluoromethylphenylboronic acid

Product 1

HCID 59229504HCID 59229504, compoundYield 83.3%

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 80711,2-DimethoxyethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 3-methyl-4-nitrobenzyl chloride (0.27 g), 3,5-bis-(trifluoromethyl)phenylboronic acid (0.45 g), tetrakis(triphenylphosfine)palladium (0.1 g) and sodium carbonate (0.48 g) in water (2 ml) and 1,2-dimethoxyethane (10 ml) was stirred under an argon atmosphere at 85° C. for 2 hours. After cooling, the reaction solution was diluted with ethyl acetate and further stirred for 10 minutes by adding water thereto. After washing the organic layer with a saturated salt solution, it was dried over anhydrous magnesium sulfate. The solution was distilled off under reduced pressure and the resultant residue was purified by silica gel column chromatography to obtain 4-(3,5-bis-trifluoromethyl-benzyl)-2-methyl-nitrobenzene (0.44 g).

Workup

  1. temperatureAfter cooling
  2. washAfter washing the organic layer with a saturated salt solution, it
  3. dry with materialwas dried over anhydrous magnesium sulfate
  4. distillationThe solution was distilled off under reduced pressure
  5. customthe resultant residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-8c6e98deb47f4c6d8b0369cd3fdafd97
Source dataset
uspto-grants-2012_02
Patent number
US08110689B2

Linked notes

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