Dimethyl Sulfoxide → 1-Bromo-3-tert-butyl-2-methoxy-5-methylbenzene

HRID 2077628Notes

Reaction equation

HRID 2077628 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[C:4]([C:9]([CH3:12])([CH3:11])[CH3:10])[C:3]=1[OH:13].[OH-].[K+].[CH3:16]S(C)=O.IC>C(OCC)C>[Br:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[C:4]([C:9]([CH3:10])([CH3:12])[CH3:11])[C:3]=1[O:13][CH3:16]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 6328Methyl iodideHCID 14797Potassium HydroxideHCID 109884772-Bromo-4-methyl-6-tert-butylphenol

Product 1

HCID 6178701-Bromo-3-tert-butyl-2-methoxy-5-methylbenzeneYield 82.8%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
0 °C

Procedure

A 500 mL three-necked round-bottomed flask was charged with 2-bromo-6-tert-butyl-4-methylphenol (20.0 g, 82.3 mmol), potassium hydroxide (9.7 g, 164.5 mmol) and DMSO (dimethylsulfoxide) (100 mL), and the mixture was chilled to 0° C. After slowly injecting iodomethane (23.4 g, 164.5 mmol) thereto, the resultant mixture was stirred at ambient temperature for 12 hours. The reaction mixture was then poured into ice (200 g), and the resultant mixture stirred for 30 minutes. After adding diethyl ether, the organic layer was isolated and the residue was extracted with diethyl ether. The combined organic layer was dried over magnesium sulfate, and evaporated to remove volatiles. Recrystallization from mixture of hexane and dichloromethane gave 1-bromo-3-tert-butyl-2-methoxy-5-methylbenzene (17.5 g, yield: 82.8%).

Workup

  1. customthe organic layer was isolated
  2. extractionthe residue was extracted with diethyl ether
  3. dry with materialThe combined organic layer was dried over magnesium sulfate
  4. customevaporated
  5. customto remove volatiles
  6. customRecrystallization
  7. additionfrom mixture of hexane and dichloromethane

Sources & evidence

ORD record
ord-bac5efd3069b40048f3f4041b06d84b0
Source dataset
uspto-grants-2011_04
Patent number
US07928173B2

Reaction notes

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