Dimethylformamide → 3-Cyano-4-isopropoxybenzoyl chloride

HRID 2189799Notes

Reaction equation

HRID 2189799 reaction equation
[C:1](Cl)(=O)[C:2]([Cl:4])=[O:3].[C:7]([C:9]1[CH:10]=C([CH:15]=[CH:16][C:17]=1[O:18][CH:19]([CH3:21])[CH3:20])C(O)=O)#[N:8].CN(C=O)C>C(Cl)Cl>[C:7]([C:9]1[CH:10]=[C:1]([CH:15]=[CH:16][C:17]=1[O:18][CH:19]([CH3:21])[CH3:20])[C:2]([Cl:4])=[O:3])#[N:8]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 21956832RP-101124

Product 1

HCID 575058423-Cyano-4-isopropoxybenzoyl chlorideYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Oxalyl chloride (0.224 ml, 2.56 mmol) was added to a stirred solution of 3-cyano-4-[(1-methylethyl)oxy]benzoic acid (which can be prepared as described in WO2005/58848, 500 mg, 2.437 mmol) in DCM (10 ml), followed by DMF (20 μl) and the resulting mixture was stirred at room temperature for 2 h. The solvent was evaporated to give the title compound (545 mg, 100%) as an olive green solid which was used in the next step without further purification.

Workup

  1. customThe solvent was evaporated

Sources & evidence

ORD record
ord-fd75616c9a8745dd88c76fe5c4c19824
Source dataset
uspto-grants-2012_12
Patent number
US08324254B2

Reaction notes

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