Bromine → 5-Bromo-3-methylthiophene-2-carbaldehyde

HRID 1157144Notes

Reaction equation

HRID 1157144 reaction equation
[CH3:1][C:2]1[CH:6]=[CH:5][S:4][C:3]=1[CH:7]=[O:8].[Br:9]Br>ClCCl>[Br:9][C:5]1[S:4][C:3]([CH:7]=[O:8])=[C:2]([CH3:1])[CH:6]=1

Participants

4

Reactant 2

HCID 24408BromineHCID 799113-Methyl-2-thiophenecarboxaldehyde

Product 1

HCID 151154075-Bromo-3-methylthiophene-2-carbaldehydeYield 90.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 3-methylthiophene-2-carbaldehyde (10 g, 0.079 mol) in dichloromethane (10 ml) was added dropwise to a stirred solution of bromine (4.08 ml, 0.079 mol) in dichloromethane (15 ml) at room temperature. The resulting mixture was heated to reflux temperature for 3 hours before cooling to room temperature, washed with water (3×50 ml), saturated NaHCO3 solution (2×25 ml), dried (MgSO4) and the solvent removed at reduced pressure to give the sub-title compound as a brown solid (14.7 g, 66% yield): 1H NMR (400 MHz, CDCl3) δH 2.60 (3H, s), 6.97 (1H, s) 9.20 (1H, s).

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureto reflux temperature for 3 hours
  3. washwashed with water (3×50 ml), saturated NaHCO3 solution (2×25 ml)
  4. dry with materialdried (MgSO4)
  5. customthe solvent removed at reduced pressure

Sources & evidence

ORD record
ord-6380b88e215b41c39f8219d727db8355
Source dataset
uspto-grants-2010_10
Patent number
US07807659B2

Reaction notes

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