Hydrogen Bromide → Methyl 5-(bromomethyl)-4-methylthiophene-2-carboxylate

HRID 69086

Reaction equation

HRID 69086 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([C:7]([O:9][CH3:10])=[O:8])[S:5][CH:6]=1.[BrH:11].OS(O)(=O)=O.[CH2:17]=O>ClCCl.O.[Zn+2].[Br-].[Br-]>[Br:11][CH2:17][C:6]1[S:5][C:4]([C:7]([O:9][CH3:10])=[O:8])=[CH:3][C:2]=1[CH3:1]

Participants

8

Reactant 4

HCID 260Hydrogen BromideHCID 712FormaldehydeHCID 1118Sulfuric AcidHCID 2777593Methyl 4-methylthiophene-2-carboxylate

Product 1

HCID 67235212Methyl 5-(bromomethyl)-4-methylthiophene-2-carboxylate

Reagents, catalysts & solvents 3

HCID 10421208Zinc bromideCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of methyl 4-methylthiophene-2-carboxylate (2.7 g, 6.4 mmol) in dichloromethane (20 mL) is added 48% aq. HBr (12 mL), H2SO4 (6 mL), ZnBr2 (5.4 g), and HCHO (2.2 mL, 37%) at 0-5° C. The mixture is stirred at room temperature for 16 hours. The solution is diluted with water, extracted with dichloromethane, washed with NaHCO3 solution, saturated brine solution, water, dried over sodium sulfate, and concentrated to give the title compound as an off white solid (3.5 g, 81%).

Workup

  1. extractionextracted with dichloromethane
  2. washwashed with NaHCO3 solution, saturated brine solution, water
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-75a3a1029acb46478cf275d50c0806ed
Source dataset
uspto-grants-2014_09
Patent number
US08822486B2

Linked notes

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