Benzoyl Peroxide → HCID 66893431, compound

HRID 1162071Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH3:9])=[CH:5][C:4]=1[S:10]([C:13]1[CH:14]=[C:15]([C:22]([O:24][CH3:25])=[O:23])[C:16]2[O:20][CH2:19][CH2:18][C:17]=2[CH:21]=1)(=[O:12])=[O:11].BrN1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>ClC1C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH3:9])=[CH:5][C:4]=1[S:10]([C:13]1[CH:14]=[C:15]([C:22]([O:24][CH3:25])=[O:23])[C:16]2[O:20][CH:19]=[CH:18][C:17]=2[CH:21]=1)(=[O:11])=[O:12]

Participants

Conditions

Temperature: 100 °C

Procedure

Methyl 5-[(2-methoxy-5-methylphenyl)sulfonyl]-2,3-dihydro-1-benzofuran-7-carboxylate (879 mg, 2.4 mmol; Intermediate 66) was dissolved in chlorobenzene (6 mL). N-bromosuccinimide (432 mg, 2.4 mmol) and benzoyl peroxide (58 mg, 0.24 mmol) were added and the mixture was stirred at 100° C. for 17 h. The mixture was washed with saturated aqueous NaHCO3 and the organic layer was concentrated. Yield: 405 mg (46%) after purification by preparative HPLC (System F; 40-60% MeCN). MS (ESI+) for C18H16O6S m/z 361 (M+H)+.

Workup

washThe mixture was washed with saturated aqueous NaHCO3
concentrationthe organic layer was concentrated
customYield: 405 mg (46%) after purification by preparative HPLC (System F; 40-60% MeCN)

Sources & evidence

ORD record: ord-50b7b58b2472489db228e6f8ed27932b
Source dataset: uspto-grants-2010_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07820675B2

Reaction notes

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