Toluene → 3-(2-Bromoethoxy)-4-methylthiophene

HRID 1004728Notes

Reaction equation

HRID 1004728 reaction equation
[CH3:1][O:2][C:3]1[C:7]([CH3:8])=[CH:6][S:5][CH:4]=1.C1(C)C=CC=CC=1.[Br:16][CH2:17]CO.OS([O-])(=O)=O.[Na+]>CO>[Br:16][CH2:17][CH2:1][O:2][C:3]1[C:7]([CH3:8])=[CH:6][S:5][CH:4]=1

Participants

6

Reactant 4

HCID 1140TolueneHCID 108982-BromoethanolHCID 516919Sodium BisulfateHCID 130618593-Methoxy-4-methylthiophene

Product 1

HCID 220163383-(2-Bromoethoxy)-4-methylthiopheneYield 55%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

4.2 g of 3-methoxy-4-methylthiophene was added to a mixture of 40 mL of toluene, 8.2 g of 2-bromo-1-ethanol (Aldrich) and 500 mg of NaHSO4. The resulting mixture was heated until the produced methanol had been distilled off and the temperature rose to 110° C. The product was cooled and washed several times with water and, subsequently, extracted with diethyl ether. The organic phase was dried with magnesium sulfate and then evaporated. The product was purified by column chromatography using silica gel and hexanes as eluent. Yield=55%.

Workup

  1. distillationhad been distilled off
  2. customrose to 110° C
  3. temperatureThe product was cooled
  4. washwashed several times with water
  5. extractionsubsequently, extracted with diethyl ether
  6. dry with materialThe organic phase was dried with magnesium sulfate
  7. customevaporated
  8. customThe product was purified by column chromatography

Sources & evidence

ORD record
ord-51ba08416c1b46cba85097dc2d86280d
Source dataset
uspto-grants-2000_04
Patent number
US06051679

Reaction notes

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