Thionyl Chloride → 4-Bromo-3-methylthiophene-2-carbonyl chloride

HRID 1386125Notes

Reaction equation

HRID 1386125 reaction equation
[Br:1][C:2]1[C:3]([CH3:10])=[C:4]([C:7](O)=[O:8])[S:5][CH:6]=1.S(Cl)([Cl:13])=O>CN(C=O)C.ClCCCl>[Br:1][C:2]1[C:3]([CH3:10])=[C:4]([C:7]([Cl:13])=[O:8])[S:5][CH:6]=1

Participants

5

Reactant 2

HCID 24386Thionyl ChlorideHCID 27570734-Bromo-3-methylthiophenecarboxylic acid

Product 1

HCID 27570744-Bromo-3-methylthiophene-2-carbonyl chlorideYield 100.2%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 111,2-DichloroethaneSolvent

Procedure

A slurry of 1.11 g (5 mmole) of 4-bromo-3-methyl-2-thiophenecarboxylic acid, 0.44 mL (6 mmole) of thionyl chloride, 5 drops of DMF, and 10 mL of 1,2-dichloroethane was heated at 800° C. for 1.5 h. The clear solution was cooled and concentrated on a roto-evaporator. The residue was dissolved in 5 mL of 1,2-dichloroethane and reconcentrated on a roto-evaporator to give 1.2 g of a tan solid, 97% pure (GC area). This acid chloride was used without further purification.

Workup

  1. temperatureThe clear solution was cooled
  2. concentrationconcentrated on a roto-evaporator
  3. dissolutionThe residue was dissolved in 5 mL of 1,2-dichloroethane
  4. customreconcentrated on a roto-evaporator

Sources & evidence

ORD record
ord-bab0636562624515b2f3def53f840a75
Source dataset
uspto-grants-2001_07
Patent number
US06265424B1

Reaction notes

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