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

HRID 1464315Notes

Reaction equation

HRID 1464315 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([Cl:12])[C:10]=1[CH3:11])[C:5](O)=[O:6].S(Cl)([Cl:15])=O.CN(C)C=O>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([Cl:12])[C:10]=1[CH3:11])[C:5]([Cl:15])=[O:6]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 185332343,5-Dichloro-4-methylbenzoic acid2×

Product 1

HCID 111279193,5-Dichloro-4-methylbenzoyl chlorideYield 110.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 3,5-dichloro-4-methylbenzoic acid (230 g, 1.12 moles), thionyl chloride (204 g, 1.71 moles), and dimethylformamide (30 milliliters(ml), in toluene (1 liter) was slowly warmed to 70° C. and stirred at that temperature for 2 hours. The toluene was eliminated in the rotavap to yield 276 g of 3,5-dichloro-4-methylbenzoyl chloride, used in the next step as such.

Sources & evidence

ORD record
ord-773d0d4220c64bf882ca5bd1cb3030bd
Source dataset
uspto-grants-1994_04
Patent number
US05304572

Reaction notes

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