Thiosulfate ion → (2-Amino-3-hydroxy-phenyl)-(4-isopropyl-phenyl)-methanone

HRID 445155Notes

Reaction equation

HRID 445155 reaction equation
[NH2:1][C:2]1[C:7]([O:8]C)=[CH:6][CH:5]=[CH:4][C:3]=1[C:10]([C:12]1[CH:17]=[CH:16][C:15]([CH:18]([CH3:20])[CH3:19])=[CH:14][CH:13]=1)=[O:11].B(Br)(Br)Br.S([O-])([O-])(=O)=S>ClCCl>[NH2:1][C:2]1[C:7]([OH:8])=[CH:6][CH:5]=[CH:4][C:3]=1[C:10]([C:12]1[CH:13]=[CH:14][C:15]([CH:18]([CH3:20])[CH3:19])=[CH:16][CH:17]=1)=[O:11]

Participants

5

Reactant 3

HCID 1084Thiosulfate ionHCID 25134Boron tribromideHCID 60112833(2-Amino-3-methoxy-phenyl)-(4-isopropyl-phenyl)-methanone

Product 1

HCID 60112845(2-Amino-3-hydroxy-phenyl)-(4-isopropyl-phenyl)-methanone

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 0.5 g (1.64 mmol) (2-amino-3-methoxy-phenyl)-(4-isopropyl-phenyl)-methanone in 5 ml dichloromethane is added under inert atmosphere 3.3 ml (3.3 mmol) 1M solution of BBr3 in dichloromethane. After stirring for 48 h the reaction mixture is poured onto 1M aqueous thiosulfate solution and extracted with dichloromethane to yield (2-amino-3-hydroxy-phenyl)-(4-isopropyl-phenyl)-methanone.

Workup

  1. extractionextracted with dichloromethane

Sources & evidence

ORD record
ord-d65fff9fc6804538880e308fefe0aef9
Source dataset
uspto-grants-2013_07
Patent number
US08476286B2

Reaction notes

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