5-Bromo-2-chlorobenzoic acid → 5-Bromo-2-chlorobenzoyl chloride

HRID 1625774Notes

Reaction equation

HRID 1625774 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([Cl:11])=[C:6]([CH:10]=1)[C:7](O)=[O:8].C(Cl)(=O)C([Cl:15])=O>ClCCl.CN(C)C=O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([Cl:11])=[C:6]([CH:10]=1)[C:7]([Cl:15])=[O:8]

Participants

5

Reactant 2

HCID 331275-Bromo-2-chlorobenzoic acidHCID 65578Oxalyl chloride

Product 1

HCID 27568715-Bromo-2-chlorobenzoyl chloride

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

5-Bromo-2-chlorobenzoic acid (5.00 g) was suspended in dichloromethane (10 ml), and thereto were added oxalyl chloride (2.2 ml) and N,N-dimethylformamide (2 drops). The mixture was stirred at room temperature for 6 hours. The solvent was evaporated under reduced pressure to give 5-bromo-2-chlorobenzoyl chloride. This compound and 2-ethylthiophene (2.38 g) were dissolved in dichloromethane (20 ml), and thereto was added aluminum chloride (3.11 g) at 0° C. The mixture was stirred at the same temperature for one hour.

Workup

  1. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-57d2634168fb4831aa03e78a15ff0a20
Source dataset
uspto-grants-2014_07
Patent number
US08785403B2

Reaction notes

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