Methyl iodide → 2-(1,1-Dimethyldecyl)-4-bromo anisole

HRID 345877Notes

Reaction equation

HRID 345877 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[C:4]([C:9]([CH3:20])([CH3:19])[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])[CH:3]=1.[H-].[Na+].[CH3:23]I>C1COCC1>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:23])=[C:4]([C:9]([CH3:19])([CH3:20])[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])[CH:3]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 136335564-Bromo-2-(1,1-dimethyldecyl) phenol

Product 1

HCID 136335572-(1,1-Dimethyldecyl)-4-bromo anisole

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The compound obtained above in part (a), (30.85 g, 90 mmoles), is dissolved in 100 ml of dry THF and then treated with 2.7 g (90 mmoles) of sodium hydride (80% in oil) which is added in small fractions. At the end of the addition, the mixture is stirred for 30 minutes at ambient temperature. 12.8 g (90 mmole) of methyl iodide are then added and this mixture is stirred for 2 hours at 20° C. The solvent is evaporated and the residue is purified by chromatography on a silica column (eluant: a mixture of dichloromethane, 40% and hexane, 60%).

Workup

  1. additionis added in small fractions
  2. additionAt the end of the addition
  3. stirringthis mixture is stirred for 2 hours at 20° C
  4. customThe solvent is evaporated
  5. customthe residue is purified by chromatography on a silica column (eluant
  6. additiona mixture of dichloromethane, 40% and hexane, 60%)

Sources & evidence

ORD record
ord-e5e7bdcde0924c0495cb07c70cbadd30
Source dataset
uspto-grants-1991_10
Patent number
US05059621

Reaction notes

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