4-Bromotoluene → HCID 68707992, compound

HRID 2376294Notes

Reaction equation

HRID 2376294 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][CH:3]=1.C([Li])CCC.CCCCCC.[NH2:20][C:21]1[C:22]([CH3:35])=[C:23]([CH3:34])[C:24]2[O:28][C:27]([CH3:30])([CH3:29])[C:26](=[O:31])[C:25]=2[C:32]=1[CH3:33]>C1COCC1.O>[NH2:20][C:21]1[C:22]([CH3:35])=[C:23]([CH3:34])[C:24]2[O:28][C:27]([CH3:29])([CH3:30])[C:26]([C:2]3[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][CH:3]=3)([OH:31])[C:25]=2[C:32]=1[CH3:33]

Participants

7

Reactant 4

HCID 78054-BromotolueneHCID 8058HexaneHCID 23114216HCID 23114216, compoundHCID 178418339Butyllithium

Product 1

HCID 68707992HCID 68707992, compoundYield 65%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 4-bromotoluene (2.73 g, 16.0 mmol) in THF (30 mL) was added dropwise a solution of n-butyllithium in hexane (1.60 M, 10.0 mL, 16.0 mmol) under argon atmosphere at −78° C., and the mixture was stirred at the same temperature for 30 minutes. Then, to the reaction solution was added dropwise a solution of 5-amino-2,2,4,6,7-pentamethyl-1-benzofuran-3 (2H)-one obtained in Reference Example 57 (1.0 g, 4.56 mmol) in THF (10 mL) at the same temperature, and the reaction solution was stirred at room temperature for 1 hour, followed by addition of water, which was extracted with ethyl acetate. The organic layer was washed with water and saturated brine, dried over anhydrous sodium sulfate and then concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=10:1), to obtain 921 mg (yield 65%) of the title compound. Melting point: 165-166° C. (ethyl acetate-hexane).

Workup

  1. stirringthe reaction solution was stirred at room temperature for 1 hour
  2. extractionwas extracted with ethyl acetate
  3. washThe organic layer was washed with water and saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=10:1)

Sources & evidence

ORD record
ord-55501d90b9664caeb3128d1c5fb8595c
Source dataset
uspto-grants-2008_12
Patent number
US07465815B2

Reaction notes

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