2,6-Di-tert-butyl-4-methylphenol → Phenol, 4-(bromomethyl)-2,6-bis(1,1-dimethylethyl)-

HRID 1656440Notes

Reaction equation

HRID 1656440 reaction equation
[C:1]([C:5]1[CH:10]=[C:9]([CH3:11])[CH:8]=[C:7]([C:12]([CH3:15])([CH3:14])[CH3:13])[C:6]=1[OH:16])([CH3:4])([CH3:3])[CH3:2].[Br:17]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl>[Br:17][CH2:11][C:9]1[CH:10]=[C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])[C:6]([OH:16])=[C:7]([C:12]([CH3:15])([CH3:14])[CH3:13])[CH:8]=1

Participants

4

Reactant 2

HCID 314042,6-Di-tert-butyl-4-methylphenolHCID 67184N-bromobutanimide

Product 1

HCID 612973Phenol, 4-(bromomethyl)-2,6-bis(1,1-dimethylethyl)-

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of 2,6-di-tert-butyl-4-methylphenol (2.34 g), N-bromosuccinimide (1.88 g) and carbon tetrachloride (25 ml) was refluxed for 2 hrs. The mixture was filtered to remove the insoluble precipitate to give a solution of 4-bromomethyl-2,6-di-tert-butylphenol. To the solution was added 3-amino-4-(2-chlorophenyl)-6,8-dimethylquinoline (2.0 g), and the whole was stirred for 5 hrs. at room temperature. The mixture was diluted with chloroform, washed with water, dried over anhydrous magnesium sulfate and distilled to remove the solvent. The residue was purified by a column chromatography on silica gel and recrystallized from a mixture of acetone and isopropyl ether to give 4-(2-chlorophenyl)-3-(2,6-di-tert-butyl-4-hydroxyphenyl)amino-6,8-dimethylquinoline as colorless prisms (1.59 g, 44.9%). m.p. 183°-185° C.

Workup

  1. temperaturewas refluxed for 2 hrs
  2. filtrationThe mixture was filtered
  3. customto remove the insoluble precipitate

Sources & evidence

ORD record
ord-0cbcefbe59c44f7589583dde78140ec7
Source dataset
uspto-grants-1993_10
Patent number
US05254565

Reaction notes

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