Allyl bromide → HCID 14085935, compound

HRID 724267Notes

Reaction equation

HRID 724267 reaction equation
[CH2:1](Br)[CH:2]=[CH2:3].[CH:5]1[C:10]([OH:11])=[CH:9][C:8]2[O:12][C:13]([S:15][C:7]=2[CH:6]=1)=[O:14].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH2:1]([O:11][C:10]1[CH:5]=[CH:6][C:7]2[S:15][C:13](=[O:14])[O:12][C:8]=2[CH:9]=1)[CH:2]=[CH2:3]

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 721396-Hydroxy-1,3-benzoxathiol-2-one

Product 1

HCID 14085935HCID 14085935, compoundYield 77.4%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Allyl bromide (28.3 ml, 0.327 mol) was added to a mixture of tioxolone (50 g, 0.297 mol) and potassium carbonate (82 g, 0.595 mol) in acetone (300 ml), and the resultant suspension stirred at RT overnight. After removal of the solvent in vacuo, the residue was partioned between EtOAc (700 ml) and water (500 ml). The aqueous phase was removed, extracted with further EtOAc (2×300 ml), and the combined organics dried over MgSO4 and concentrated to an off-white solid (66.6 g). Purification by flash column chromatography on silica eluting with EtOAc:pentane (1:39 to 1:9) gave the title compound as a white solid (48.3 g, 0.23 mol).

Workup

  1. customAfter removal of the solvent in vacuo
  2. customThe aqueous phase was removed
  3. extractionextracted with further EtOAc (2×300 ml)
  4. dry with materialthe combined organics dried over MgSO4
  5. concentrationconcentrated to an off-white solid (66.6 g)
  6. customPurification by flash column chromatography on silica eluting with EtOAc:pentane (1:39 to 1:9)

Sources & evidence

ORD record
ord-581c8cd0f42a49e29540832801fbeacd
Source dataset
uspto-grants-2006_11
Patent number
US07141586B2

Reaction notes

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