Oxalyl chloride → 3-(1-Cyanocyclopropyl)benzoyl chloride

HRID 2190366Notes

Reaction equation

HRID 2190366 reaction equation
[C:1]([C:3]1([C:6]2[CH:7]=[C:8]([CH:12]=[CH:13][CH:14]=2)[C:9](O)=[O:10])[CH2:5][CH2:4]1)#[N:2].C(Cl)(=O)C([Cl:18])=O>O1CCCC1.CN(C)C=O>[C:1]([C:3]1([C:6]2[CH:7]=[C:8]([CH:12]=[CH:13][CH:14]=2)[C:9]([Cl:18])=[O:10])[CH2:5][CH2:4]1)#[N:2]

Participants

5

Reactant 2

HCID 65578Oxalyl chlorideHCID 574410393-(1-Cyanocyclopropyl)benzoic acid

Product 1

HCID 866319823-(1-Cyanocyclopropyl)benzoyl chloride

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-(1-cyanocyclopropyl)benzoic acid (10.0 g, 53.4 mmol) produced in Example A1(iii) in tetrahydrofuran (130 mL) were added oxalyl chloride (5.47 mL, 64.1 mmol) and N,N-dimethylformamide (2 drops), and the mixture was stirred at room temperature for 3 hr. The reaction mixture was concentrated under reduced pressure to give 3-(1-cyanocyclopropyl)benzoyl chloride as a colorless oil.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure

Sources & evidence

ORD record
ord-b31fa846190d455aabe744e1e42f6f43
Source dataset
uspto-grants-2012_12
Patent number
US08324395B2

Reaction notes

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