Oxalyl chloride → 3-(1,3-Dioxo-1,3-dihydro-2H-isoindol-2-yl)-4,4,4-trifluorobutanoyl chloride

HRID 539977Notes

Reaction equation

HRID 539977 reaction equation
[O:1]=[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=[O:11])[N:3]1[CH:12]([C:17]([F:20])([F:19])[F:18])[CH2:13][C:14](O)=[O:15].C(Cl)(=O)C([Cl:24])=O>ClCCl.CN(C)C=O>[O:1]=[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=[O:11])[N:3]1[CH:12]([C:17]([F:20])([F:19])[F:18])[CH2:13][C:14]([Cl:24])=[O:15]

Participants

5

Reactant 2

HCID 65578Oxalyl chlorideHCID 712550843-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-4,4,4-trifluorobutanoic acid

Product 1

HCID 866913733-(1,3-Dioxo-1,3-dihydro-2H-isoindol-2-yl)-4,4,4-trifluorobutanoyl chlorideYield 97.5%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-4,4,4-trifluorobutanoic acid (270 mg, 0.94 mmol) in dichloromethane (10 mL) was added oxalyl chloride (0.16 mL, 1.88 mmol), followed by N,N-dimethylformamide (1 drop). After the gas ceased to produce, the reaction mixture was stirred at room temperature for 2 hours. After the mixture was concentrated in vacuo, the residue was diluted with dichloromethane and concentrated in vacuo again to afford 280 mg of the product (yield was 90%), which was used for next step without purification.

Workup

  1. customto produce
  2. concentrationAfter the mixture was concentrated in vacuo
  3. additionthe residue was diluted with dichloromethane
  4. concentrationconcentrated in vacuo again

Sources & evidence

ORD record
ord-6c53b9fcb39d443fa11372ea62a1f37a
Source dataset
uspto-grants-2014_10
Patent number
US08871756B2

Reaction notes

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