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

HRID 1517921ノート

反応式

HRID 1517921 の反応式
[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]

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 3283Diethyl Ether溶媒

反応条件

温度
0 °C

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-918967de911c4a698dddda70ddb7b0b2
出典データセット
uspto-grants-2012_07
特許番号
US08232359B2

反応ノート

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