Azobisisobutyronitrile → 2-(4-Bromomethyl-thiophen-3-ylmethyl)-isoindole-1,3-dione

HRID 1592658Notes

Reaction equation

[CH3:1][CH:2]1[CH2:6][S:5][CH2:4][CH:3]1[CH2:7][N:8]1[C:16](=[O:17])[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9]1=[O:18].C1C(=O)N([Br:26])C(=O)C1.CC(N=NC(C#N)(C)C)(C#N)C>C(Cl)(Cl)(Cl)Cl>[Br:26][CH2:1][C:2]1[C:3]([CH2:7][N:8]2[C:16](=[O:17])[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[C:9]2=[O:18])=[CH:4][S:5][CH:6]=1

Participants

Conditions

Temperature: 85 °C

Procedure

2-(4-Methyl-tetrahydro-thiophen-3-ylmethyl)-isoindole-1,3-dione (410.0 mg, 1.59 mmol) and NBS (312.0 mg, 1.75 mmol) were dissolved in CCl4 (8.0 mL). AIBN (100 mg) was added in one portion. The mixture was heated at 85° C. under N2 for 90 min. After cooling down, the mixture was passed through a short silica gel column (4×10 cm), eluted with CH2Cl2. The solution obtained was concentrated and the residue was recrystallized from EtOAc/Hexanes (5/1) to give 2-(4-Bromomethyl-thiophen-3-ylmethyl)-isoindole-1,3-dione (285 mg, 50%) as a white solid. 1H NMR (CDCl3) δ 4.74 (s, 2H), 4.91 (s, 2H), 7.29-7.30 (d, 1H, J=3.3 Hz), 7.70-7.71 (d, 1H, J=3.3 Hz), 7.70-7.73 (m, 2H), 7.82-7.87 (m, 2H).

Workup

temperatureAfter cooling down
washeluted with CH2Cl2
customThe solution obtained
concentrationwas concentrated
customthe residue was recrystallized from EtOAc/Hexanes (5/1)

Sources & evidence

ORD record: ord-19ecddc462ce41858596f49969b292a3
Source dataset: uspto-grants-2007_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07291631B2

Reaction notes

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