Reaction #1453373

Reaction equation

3-Methyl-thiophene-2-carboxylic acid methyl ester

NBS

water

→

title compound

Yield 89.1%

3-Bromomethyl-thiophene-2-carboxylic acid methyl ester

Yield 89.1%

Solvents

CCl4

Conditions

Workup

1. 1
   TemperatureThe reaction mixture is refluxed for 6 hours
2. 2
   Extractionthe mixture is extracted with EtOAc (3×)
3. 3
   DryingThe organic layers are dried over MgSO4
4. 4
   Filtrationfiltered
5. 5
   Concentrationconcentrated
6. 6
   OtherThe crude product is purified by silica gel column chromatography
7. 7
   Washeluting with 98:2 petroleum ether-EtOAc

Procedure

3-Methyl-thiophene-2-carboxylic acid methyl ester (1 g, 6.4 mmol) is dissolved in CCl4 (15 mL), and NBS (1.19 g, 6.7 mmol) and benzoyl peroxide (15 mg) are added. The reaction mixture is refluxed for 6 hours, then water is added and the mixture is extracted with EtOAc (3×). The organic layers are dried over MgSO4, filtered and concentrated. The crude product is purified by silica gel column chromatography eluting with 98:2 petroleum ether-EtOAc to give the title compound (1.34 g, 27%).

Source