Thiosulfate ion → 5-Bromo-4-methylisobenzofuran-1(3H)-one

HRID 1848555Notes

Reaction equation

HRID 1848555 reaction equation
[CH3:1][C:2]1[C:10]([Sn](C)(C)C)=[CH:9][CH:8]=[C:7]2[C:3]=1[CH2:4][O:5][C:6]2=[O:15].[Br:16]Br.S([O-])([O-])(=O)=S>C(Cl)Cl>[Br:16][C:10]1[C:2]([CH3:1])=[C:3]2[C:7](=[CH:8][CH:9]=1)[C:6](=[O:15])[O:5][CH2:4]2

Participants

5

Reactant 3

HCID 1084Thiosulfate ionHCID 24408BromineHCID 89941073HCID 89941073, compound

Product 1

HCID 595687115-Bromo-4-methylisobenzofuran-1(3H)-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 4-methyl-5-(trimethylstannyl)isobenzofuran-1(3H)-one (4.37 g, 14.05 mmol) in DCM (20 mL) was added bromine (0.796 ml, 15.46 mmol) at 0° C. The reaction mixture was stirred at 0° C. for 0.5 h. Saturated thiosulfate solution was added and the mixture was extracted with methylene chloride (2×100 mL), the combined organic phase was dried over sodium sulfate, concentrated to give 5-bromo-4-methylisobenzofuran-1(3H)-one. LC/MS: (M+1)+: 226.89; 228.89.

Workup

  1. extractionthe mixture was extracted with methylene chloride (2×100 mL)
  2. dry with materialthe combined organic phase was dried over sodium sulfate
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-699b232888c5419e86d7a308fa1f1c40
Source dataset
uspto-grants-2015_02
Patent number
US08952166B2

Reaction notes

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