Dimethylformamide → 2-Chloro-6-methylbenzoyl chloride

HRID 1626929Notes

Reaction equation

HRID 1626929 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]([CH3:11])[C:3]=1[C:4](O)=[O:5].CN(C=O)C.C(Cl)(=O)C([Cl:20])=O>C(Cl)Cl>[Cl:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]([CH3:11])[C:3]=1[C:4]([Cl:20])=[O:5]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 888702-Chloro-6-methylbenzoic acid

Product 1

HCID 223820402-Chloro-6-methylbenzoyl chloride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-chloro-6-methylbenzoicacid (339) (300 g, 1.76 mol, 1.0 eq) and DMF (0.5 mL) in DCM (500 mL) at RT, oxalyl chloride (249 g, 1.92 mol, 1.1 eq) was added slowly (over 5 min). The resulting mixture was stirred at RT for 2 h and then concentrated in vacuo to afford 2-chloro-6-methylbenzoyl chloride (340) which was used directly in the next step.

Workup

  1. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-26617822c2144a4ea32832d561d61e2b
Source dataset
uspto-grants-2014_07
Patent number
US08785470B2

Reaction notes

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