Dimethylformamide → 3,5-Dichloro-4-formylbenzoyl chloride

HRID 1656486Notes

Reaction equation

HRID 1656486 reaction equation
[CH:1]([C:3]1[C:11]([Cl:12])=[CH:10][C:6]([C:7](O)=[O:8])=[CH:5][C:4]=1[Cl:13])=[O:2].S(Cl)([Cl:16])=O.CN(C)C=O>C1(C)C=CC=CC=1>[CH:1]([C:3]1[C:11]([Cl:12])=[CH:10][C:6]([C:7]([Cl:16])=[O:8])=[CH:5][C:4]=1[Cl:13])=[O:2]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 197881593,5-dichloro-4-formylbenzoic acid

Product 1

HCID 197881473,5-Dichloro-4-formylbenzoyl chlorideYield 115.8%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Conditions

Temperature
70 °C

Procedure

A mixture of 4-formyl-3,5-dichlorobenzoic acid (15.0 g, 0.06 moles), thionyl chloride (12.1 g, 0.107 moles), and dimethylformamide (5 ml) in toluene (100 ml) was slowly warmed to 70° C. and stirred at that temperature for 2 hours. The toluene was eliminated in the rotavap to yield 16.5 g of 4-formyl-3,5-dichlorobenzoyl chloride used in the next step as such.

Sources & evidence

ORD record
ord-bdb321b1468e41af96217e976d46362c
Source dataset
uspto-grants-1993_10
Patent number
US05254584

Reaction notes

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