Methyl iodide → HCID 22048156, compound

HRID 895200Notes

Reaction equation

HRID 895200 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([O:11][C:12]2[CH:17]=[CH:16][C:15](Br)=[C:14]([O:19][CH3:20])[CH:13]=2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.Br[C:22]1[CH:28]=[CH:27][C:25]([OH:26])=[CH:24][C:23]=1O.[C:30]1(C)[CH:35]=CC(S(Cl)(=O)=O)=[CH:32][CH:31]=1.C(=O)([O-])[O-].[K+].[K+].IC>CCOCC.CC(C)=O>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([O:11][C:12]2[CH:17]=[CH:16][C:15]([C:30]3[CH:31]=[CH:32][C:23]4[C:22](=[CH:28][CH:27]=[C:25]([OH:26])[CH:24]=4)[CH:35]=3)=[C:14]([O:19][CH3:20])[CH:13]=2)(=[O:10])=[O:9])=[CH:4][CH:3]=1

Participants

8

Reactant 5

HCID 6328Methyl iodideHCID 73974-Toluenesulfonyl chlorideHCID 11430Potassium CarbonateHCID 811054-BromoresorcinolHCID 117926414-Bromo-3-methoxyphenyl 4-methylbenzenesulfonate

Product 1

HCID 22048156HCID 22048156, compoundYield 70%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 3283Diethyl EtherSolvent

Procedure

4-Bromo-3-methoxyphenyl 4-methylbenzenesulfonate A mixture of 4-bromo-resorcinol (4.92 g, 26.0 mmol), p-toluenesulfonic chloride (5.95 g, 31.2 mmol), potassium carbonate (23 g, 167 mmol), and acetone (300 mL) was refluxed for 16 hr. Iodomethane (9.89 g, 70 mmol) was added and the mixture was refluxed for an additional 12 hr. The mixture was cooled to room temperature and ether (200 mL) was added and the suspension was filtered. The filtrate was stripped of solvent and purified on a silica column (10% ethyl acetate—hexanes) to yield 6.49 g (70%) of the title compound as a white solid.

Workup

  1. temperaturewas refluxed for 16 hr
  2. temperaturethe mixture was refluxed for an additional 12 hr
  3. filtrationthe suspension was filtered
  4. custompurified on a silica column (10% ethyl acetate—hexanes)

Sources & evidence

ORD record
ord-cdcb8f244c244ad3af7c73448ae8462f
Source dataset
uspto-grants-2005_07
Patent number
US06914074B2

Reaction notes

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