Dimethylformamide → 3-(1-Cyano-1-methylethyl)benzoyl chloride

HRID 1874566Notes

Reaction equation

HRID 1874566 reaction equation
[C:1]([C:3]([C:6]1[CH:7]=[C:8]([CH:12]=[CH:13][CH:14]=1)[C:9](O)=[O:10])([CH3:5])[CH3:4])#[N:2].C(Cl)(=O)C([Cl:18])=O.CN(C)C=O>O1CCCC1>[C:1]([C:3]([C:6]1[CH:7]=[C:8]([CH:12]=[CH:13][CH:14]=1)[C:9]([Cl:18])=[O:10])([CH3:5])[CH3:4])#[N:2]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 571495383-(2-Cyanopropan-2-yl)benzoic acid

Product 1

HCID 866319813-(1-Cyano-1-methylethyl)benzoyl chloride

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-(1-cyano-1-methylethyl)benzoic acid (2.66 g, 14.0 mmol) in tetrahydrofuran (28 mL) were added oxalyl chloride (1.63 mL, 19.1 mmol) and N,N-dimethylformamide (about 20 μL), and the mixture was stirred at room temperature for 1 hr. The reaction mixture was concentrated under reduced pressure to give 3-(1-cyano-1-methylethyl)benzoyl chloride as a pale-brown oil.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure

Sources & evidence

ORD record
ord-88ca02e97ca14a07bab25c0be6e3c534
Source dataset
uspto-grants-2012_11
Patent number
US08304557B2

Reaction notes

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