Dimethylformamide → 5-Bromo-2-chlorobenzoyl chloride

HRID 1913068Notes

Reaction equation

HRID 1913068 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].CN(C=O)C.S(Cl)([Cl:19])=O>C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([Cl:11])=[C:6]([CH:10]=1)[C:7]([Cl:19])=[O:8]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 331275-Bromo-2-chlorobenzoic acid

Product 1

HCID 27568715-Bromo-2-chlorobenzoyl chlorideYield 94.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
0 °C

Procedure

Under Ar protection, 5-bromo-2-chloro-benzoic acid (35 g, 148.6 mmol) was dissolved in toluene (230 ml), followed by addition of DMF (0.5 mL) at room temperature, then the reaction mixture was cooled to 0° C. The reaction mixture was heated to 100° C. after thionyl chloride (44 g, 372 mmol) was dropwise added. After 5 hours, the reaction mixture was concentrated under reduced pressure to obtain the title compound 5-bromo-2-chloro-benzoyl chloride 12n (35.5 g, pale yellow grease), yield: 94.0%.

Workup

  1. additionwas dropwise added
  2. concentrationthe reaction mixture was concentrated under reduced pressure

Sources & evidence

ORD record
ord-48e8c9d894ed47ae9467c92bcdb29e80
Source dataset
uspto-grants-2013_12
Patent number
US08609622B2

Reaction notes

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