Water → Methyl 3-(bromomethyl)thiophene-2-carboxylate

HRID 1921817Notes

Reaction equation

HRID 1921817 reaction equation
[CH3:1][O:2][C:3]([C:5]1[S:6][CH:7]=[CH:8][C:9]=1[CH3:10])=[O:4].C1C(=O)N([Br:18])C(=O)C1.O>C(Cl)(Cl)(Cl)Cl.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>[CH3:1][O:2][C:3]([C:5]1[S:6][CH:7]=[CH:8][C:9]=1[CH2:10][Br:18])=[O:4]

Participants

6

Reactant 3

HCID 962WaterHCID 67184N-bromobutanimideHCID 580757Methyl 3-methylthiophene-2-carboxylate

Product 1

HCID 10537693Methyl 3-(bromomethyl)thiophene-2-carboxylateYield 89.1%

Reagents, catalysts & solvents 2

HCID 7187Benzoyl PeroxideCatalystHCID 5943Carbon TetrachlorideSolvent

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%).

Workup

  1. temperatureThe reaction mixture is refluxed for 6 hours
  2. extractionthe mixture is extracted with EtOAc (3×)
  3. dry with materialThe organic layers are dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude product is purified by silica gel column chromatography
  7. washeluting with 98:2 petroleum ether-EtOAc

Sources & evidence

ORD record
ord-af021db97eb645ad864b632cdb96fd16
Source dataset
uspto-grants-2012_05
Patent number
US08173656B2

Reaction notes

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