3,5-Dichlorophenylboronic acid → HCID 178498930, compound

HRID 1746191Notes

Reaction equation

HRID 1746191 reaction equation
[CH3:1][O:2][C:3]([C:5]1[C:6](=[O:17])[S:7][C:8]2[C:13]([C:14]=1[OH:15])=[CH:12][CH:11]=[C:10](Br)[CH:9]=2)=[O:4].[Cl:18][C:19]1[CH:20]=[C:21](B(O)O)[CH:22]=[C:23]([Cl:25])[CH:24]=1>>[CH3:1][O:2][C:3]([C:5]1[C:6](=[O:17])[S:7][C:8]2[C:13]([C:14]=1[OH:15])=[CH:12][CH:11]=[C:10]([C:21]1[CH:20]=[C:19]([Cl:18])[CH:24]=[C:23]([Cl:25])[CH:22]=1)[CH:9]=2)=[O:4]

Participants

3

Reactant 2

HCID 27343313,5-Dichlorophenylboronic acidHCID 178498916HCID 178498916, compound

Product 1

HCID 178498930HCID 178498930, compound

Procedure

7-(3,5-Dichloro-phenyl)-4-hydroxy-2-oxo-2H-thiochromene-3-carboxylic acid methyl ester was prepared from 7-bromo-4-hydroxy-2-oxo-2H-thiochromene-3-carboxylic acid methyl ester (Example 5 e) and 3,5-dichlorophenylboronic acid under conditions analogous to Example 7(a). The crude product was purified by silica gel chromatography (eluting with 5%-60% EtOAc in CH2Cl2) to provide 7-(3,5-dichloro-phenyl)-4-hydroxy-2-oxo-2H-thiochromene-3-carboxylic acid methyl ester. MS ESI(−) m/e: 378.98 (M−1).

Workup

  1. customThe crude product was purified by silica gel chromatography (eluting with 5%-60% EtOAc in CH2Cl2)

Sources & evidence

ORD record
ord-a275caf112bf41ce9524a45ce1303a27
Source dataset
uspto-grants-2015_10
Patent number
US09149476B2

Reaction notes

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