Dimethylformamide → 2-Bromo-5-iodobenzoyl chloride

HRID 1258849Notes

Reaction equation

HRID 1258849 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][C:8]([I:11])=[CH:7][C:3]=1[C:4](O)=[O:5].C(Cl)(=O)C([Cl:15])=O.CN(C=O)C>ClCCl>[Br:1][C:2]1[CH:10]=[CH:9][C:8]([I:11])=[CH:7][C:3]=1[C:4]([Cl:15])=[O:5]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 27355722-Bromo-5-iodobenzoic acid

Product 1

HCID 583408092-Bromo-5-iodobenzoyl chlorideYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 2-bromo-5-iodobenzoic acid (25.0 g, 76.48 mmol) in dichloromethane (200 mL) was added oxalylchloride (10.3 mL, 114.74 mmol) at 0° C. followed by DMF (0.9 mL). After complete addition, the reaction mixture was stirred at room temperature for 3 h. Volatiles were evaporated under reduced pressure to furnish 2-bromo-5-iodo-benzoyl chloride (26.4 g). The crude product was used for the next step immediately.

Workup

  1. additionAfter complete addition
  2. customVolatiles were evaporated under reduced pressure

Sources & evidence

ORD record
ord-8133b0d50063454599956396d7d55dc7
Source dataset
uspto-grants-2013_06
Patent number
US08466114B2

Reaction notes

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