1,2-Bis(chloromethyl)benzene → 4-Tert-butyl-2-[5-(2-chloromethylphenylmethoxy)benzofuran-2-yl]thiazole

HRID 487680Notes

Reaction equation

HRID 487680 reaction equation
[C:1]([C:5]1[N:6]=[C:7]([C:10]2[O:11][C:12]3[CH:18]=[CH:17][C:16]([OH:19])=[CH:15][C:13]=3[CH:14]=2)[S:8][CH:9]=1)([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].[Cl:22][CH2:23][C:24]1[C:25]([CH2:30]Cl)=[CH:26][CH:27]=[CH:28][CH:29]=1>O1CCCC1>[C:1]([C:5]1[N:6]=[C:7]([C:10]2[O:11][C:12]3[CH:18]=[CH:17][C:16]([O:19][CH2:30][C:25]4[CH:26]=[CH:27][CH:28]=[CH:29][C:24]=4[CH2:23][Cl:22])=[CH:15][C:13]=3[CH:14]=2)[S:8][CH:9]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 119191,2-Bis(chloromethyl)benzeneHCID 24758Sodium hydrideHCID 108586652-(4-Tert-butylthiazol-2-yl)-5-hydroxybenzofuran

Product 1

HCID 190928204-Tert-butyl-2-[5-(2-chloromethylphenylmethoxy)benzofuran-2-yl]thiazoleYield 74.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a cooled solution of 4-tert-butyl-2-(5-hydroxybenzofuran-2-yl)thiazole (0.8 g) in tetrahydrofuran (16 ml), sodium hydride ((60% in mineral oil) 0.152 g) was added below 10° C. After being stirred for 30 minutes, α,α'-dichloroxylene (2.05 g) was added to the mixture. After subsequently being stirred at ambient temperature for 30 minutes, the mixture was refluxed for 9.5 hours. After the solvent was removed under reduced pressure, the residue was subjected to column chromatography on silica gel (25 g) and eluted with a mixture of n-hexane and toluene (1:1). The fractions containing object compound were combined and concentrated under reduced pressure to give an oil of 4-tert-butyl-2-[5-(2-chloromethylphenylmethoxy)benzofuran-2-yl]thiazole (0.9 g).

Workup

  1. stirringAfter subsequently being stirred at ambient temperature for 30 minutes
  2. temperaturethe mixture was refluxed for 9.5 hours
  3. customAfter the solvent was removed under reduced pressure
  4. washeluted with a mixture of n-hexane and toluene (1:1)
  5. additionThe fractions containing object compound
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-78e61d2f6b164f79b461a807ea116eeb
Source dataset
uspto-grants-1994_03
Patent number
US05296495

Reaction notes

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