Carbon tetrabromide → 5-[2-Bromo-4-(bromomethyl)phenyl]isothiazolidin-3-one 1,1-dioxide

HRID 724680Notes

Reaction equation

HRID 724680 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([CH2:8]O)[CH:5]=[CH:4][C:3]=1[CH:10]1[S:14](=[O:16])(=[O:15])[NH:13][C:12](=[O:17])[CH2:11]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Br)(Br)(Br)[Br:38]>O1CCOCC1.C(#N)C>[Br:1][C:2]1[CH:7]=[C:6]([CH2:8][Br:38])[CH:5]=[CH:4][C:3]=1[CH:10]1[S:14](=[O:16])(=[O:15])[NH:13][C:12](=[O:17])[CH2:11]1

Participants

6

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 218791345-[2-Bromo-4-(hydroxymethyl)phenyl]isothiazolidin-3-one 1,1-dioxide

Product 1

HCID 218795715-[2-Bromo-4-(bromomethyl)phenyl]isothiazolidin-3-one 1,1-dioxide

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of 5-[2-bromo-4-(hydroxymethyl)phenyl]isothiazolidin-3-one 1,1-dioxide (54.0 mg, 0.169 mmol) in 1,4-dioxane (5 mL) was added triphenylphosphine (49 mg, 0.18 mmol) and carbon tetrabromide (62 mg, 0.18 mmol) at room temperature. The resulting mixture was stirred at room temperature overnight. The reaction was diluted with acetonitrile and purified by preparative LCMS to give the product as a white solid.

Workup

  1. custompurified by preparative LCMS

Sources & evidence

ORD record
ord-6bfacc0dfd454ba6b48e8939f0a66060
Source dataset
uspto-grants-2006_11
Patent number
US07141596B2

Reaction notes

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