m-Chloroperbenzoic acid → 3-(3,4,5-Trimethoxyphenylsulfinyl)Biphenyl

HRID 522568Notes

Reaction equation

HRID 522568 reaction equation
[C:1]1([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:6]=[CH:5][CH:4]=[C:3]([S:7][C:8]2[CH:13]=[C:12]([O:14][CH3:15])[C:11]([O:16][CH3:17])=[C:10]([O:18][CH3:19])[CH:9]=2)[CH:2]=1.C1C=C(Cl)C=C(C(OO)=[O:34])C=1>ClCCl>[CH3:19][O:18][C:10]1[CH:9]=[C:8]([S:7]([C:3]2[CH:2]=[C:1]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH:6]=[CH:5][CH:4]=2)=[O:34])[CH:13]=[C:12]([O:14][CH3:15])[C:11]=1[O:16][CH3:17]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 53363791Biphenyl-3-yl(3,4,5-trimethoxyphenyl)sulfane

Product 1

HCID 533637933-(3,4,5-Trimethoxyphenylsulfinyl)BiphenylYield 87%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

At 0° C., to a solution of 500 mg (1.42 mmol) of compound (4a) and 5 mL of dichloromethane was added very slowly 1 equiv. of m-CPBA over 3 h. Sulfoxide formation was monitored by thin-layer chromatography. Purification was performed with a flash chromatographic column, and an amorphous powder of (4c) was obtained (87% yield). 1H NMR (500 MHz, CDCl3) δ 7.92 (br, 1H), 7.71 (d, 2H), 7.62-7.60 (m, 3H), 7.58-7.40 (m, 4H), 6.94 (s, 2H), 3.79 (s, 3H), 3.74 (s, 6H). MS (ESI) m/z 369.1 (M+H)+.

Workup

  1. customPurification

Sources & evidence

ORD record
ord-94cf6aee4d544f7cb3f13451134b60e9
Source dataset
uspto-grants-2016_05
Patent number
US09334242B2

Reaction notes

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