Thionyl Chloride → 3-Chloro-3-(4-chlorophenyl)-2-benzylisoindolin-1-one
Reaction equation
[CH:1]1[CH:6]=[CH:5][C:4]([CH2:7][N:8]2[C:17](O)([C:18]3[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][CH:19]=3)[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[C:9]2=[O:10])=[CH:3][CH:2]=1.S(Cl)([Cl:28])=O>CN(C=O)C>[Cl:28][C:17]1([C:18]2[CH:19]=[CH:20][C:21]([Cl:24])=[CH:22][CH:23]=2)[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:9](=[O:10])[N:8]1[CH2:7][C:4]1[CH:3]=[CH:2][CH:1]=[CH:6][CH:5]=1Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
Distilled THF (25 mL) was added to 2-benzyl-3-(4-chlorophenyl)-3-hydroxy-2,3-dihydroisoindolin-1-one (400 mg, 1.145 mmol), thionyl chloride (299.6 mg, 2.51 mmol, 0.18 mL) and catalytic DMF (3 drops) as for general procedure B1. 3-Chloro-3-(4-chlorophenyl)-2-benzylisoindolin-1-one was produced as a colourless oil (421 mg, 1.145 mmol) which was used immediately without further purification. Distilled THF (25 mL) was added to 3-chloro-3-(4-chlorophenyl)-2-benzylisoindolin-1-one (421 mg, 1.145 mmol), cis-cyclopentene diol (572 mg, 5.725 mmol) and potassium carbonate (792.9 mg, 5.725 mmol) as for general procedure B. Removal of the solvent yielded the crude product as a pink oil (354 mg). The sample was purified by flash column chromatography (EtOAc:Petrol, 40:60) to yield the title product as a cream oily solid (277.5 mg, 0.643 mmol, 56% yield). 1H NMR: (300 Hz, CDCl3) δ ppm 0.84, 1.66 (m, 1H, H16/H16′) 1.26 (m, 1H, H16/H16′) 3.85 (m, 1H, H17) 3.36 (m, 1H, H15) 4.15 (d, 1H, J=15.27 Hz, H9/H9′), 4.62 (d, 1H, J=15.31 Hz, H9/H9′), 4.68, 5.73 (dd, 1H, H18/H19), 5.21, 5.64 (dd, 1H, H18/H19), 7.18 (m, 10H, H1-H5, H10-H14), 7.62 (m, 2H, H6-H7), 7.83 (d, 1H, H8). Mp: 63.4-63.9° C. IR: 1489, 1683, 3061, 3379 cm−1.
Workup
- distillationDistilled THF (25 mL)
Sources & evidence
- ORD record
- ord-a396620c84a34a3984f55b95c08dbd48
- Source dataset
- uspto-grants-2013_12
- Patent number
- US08618158B2
Reaction notes
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