Thionyl Chloride → 3-Chloro-3-(4-chlorophenyl)-2-propylisoindolin-1-one

HRID 2199286Notes

Reaction equation

HRID 2199286 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2(O)[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[C:10](=[O:17])[N:9]2[CH2:18][CH2:19][CH3:20])=[CH:4][CH:3]=1.S(Cl)([Cl:24])=O>CN(C=O)C>[Cl:24][C:8]1([C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=2)[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10](=[O:17])[N:9]1[CH2:18][CH2:19][CH3:20]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 513495613-(4-Chlorophenyl)-3-hydroxy-2-propylisoindolin-1-one

Product 1

HCID 513512563-Chloro-3-(4-chlorophenyl)-2-propylisoindolin-1-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideCatalyst

Procedure

Distilled THF (5 mL) was added to 3-(4-chlorophenyl)-3-hydroxy-2-propylisoindolin-1-one (104 mg, 0.33 mmol), thionyl chloride (86.83 mg, 0.73 mmol, 0.05 mL) and catalytic DMF (3 drops) as for general procedure B1. 3-Chloro-3-(4-chlorophenyl)-2-propylisoindolin-1-one was produced as an orange oil (105 mg, 0.33 mmol) which was used immediately without further purification. Distilled THF (6 mL) was added to 3-chloro-3-(4-chlorophenyl)-2-propylisoindolin-1-one (211.2, 0.66 mmol), cis-cyclopentene diol (330 mg, 3.3 mmol) and potassium carbonate (456 mg, 3.3 mmol) as for general procedure B. Removal of the solvent yielded the crude product as a colourless oil (160.2 mg). The sample was purified by flash column chromatography (EtOAc:Petrol, 40:60) to yield the title product as an colourless viscous oil. (129 mg, 0.43 mmol, 51% yield). 1H NMR: (300 Hz, DMSO) δ ppm 0.76 (t, 3H, H11), 1.36 (m, 1H, H13/H13′), 1.49, 1.76 (m, 1H, H13/H13′), 3.12 (m, 2H H10) 3.96 (m, 1H, H9/H9′), 4.26 (m, 1H, H9/H9′), 5.29, 5.87, (dd, 1H, H15/H16) 5.74, 5.79 (dd, 1H, H15/H16) 7.23 (d, 1H,), 7.38 (m, 4H, H1-H5), 7.61 (m, 2H, H6-H7), 7.76 (d, 1H, H8). IR: 1365, 1682, 2969, 3363 cm−1.

Workup

  1. distillationDistilled THF (5 mL)

Sources & evidence

ORD record
ord-be0a7c25935141c2bf79744d5b7343c6
Source dataset
uspto-grants-2016_06
Patent number
US09358222B2

Reaction notes

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