Benzoyl Peroxide → 7-Bromo-5-[(4-methylphenyl)sulfonyl]-1-benzofuran

HRID 1162089Notes

Reaction equation

[Br:1][C:2]1[C:10]2[O:9][CH2:8][CH2:7][C:6]=2[CH:5]=[C:4]([S:11]([C:14]2[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][CH:15]=2)(=[O:13])=[O:12])[CH:3]=1.C1C(=O)N(Br)C(=O)C1.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl.CCOC(C)=O.CCCCCC>[Br:1][C:2]1[C:10]2[O:9][CH:8]=[CH:7][C:6]=2[CH:5]=[C:4]([S:11]([C:14]2[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][CH:15]=2)(=[O:13])=[O:12])[CH:3]=1

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of 7-bromo-5-[(4-methylphenyl)sulfonyl]-2,3-dihydro-1-benzofuran (353 mg, 1 mmol; Intermediate 78), NBS (178 mg, 1 mmol) and dibenzoylperoxide (24 mg, 0.1 mmol) in carbon tetrachloride (20 mL) was heated to 80° C. for 2 h. TEA (2 mL) was added and the mixture was heated for another 2 h. Flash chromatography using EtOAc/hexane 10:90→25:75 as eluent gave the title product as a white crystalline material. Yield: 130 mg (37%). 1H NMR (400 MHz, CDCl3) δ 2.39 (s, 3H), 6.93 (d, 1H), 7.30 (d, 2H), 7.78 (d, 1H), 7.84 (d, 2H), 8.02 (d, 1H), 8.19 (d, 1H).

Workup

temperaturethe mixture was heated for another 2 h

Sources & evidence

ORD record: ord-a4061574c4294728bb3601d5270ffd0b
Source dataset: uspto-grants-2010_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07820675B2

Reaction notes

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