Boron tribromide → HCID 57777377, compound

HRID 660825Notes

Reaction equation

HRID 660825 reaction equation
C([O:8][C:9]1[CH:14]=[C:13]([Cl:15])[CH:12]=[CH:11][C:10]=1[N:16]1[S:20](=[O:22])(=[O:21])[NH:19][C:18](=[O:23])[CH2:17]1)C1C=CC=CC=1.B(Br)(Br)Br>C(Cl)Cl>[Cl:15][C:13]1[CH:12]=[CH:11][C:10]([N:16]2[S:20](=[O:22])(=[O:21])[NH:19][C:18](=[O:23])[CH2:17]2)=[C:9]([OH:8])[CH:14]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 68838631HCID 68838631, compound

Product 1

HCID 57777377HCID 57777377, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 5-(2-benzyloxy-4-chlorophenyl)-1,1-dioxo-1,2,5-thiadiazolidin-3-one (388 mg, 1.1 mmol) in methylene chloride (10 mL) at 0° C. is added dropwise BBr3 (1.65 mL of 1.0M in methylene chloride, 1.65 mmol) and the mixture is stirred at 0° C. for 30 min. Ice is added and the organic phase is washed with 1N HCl. The aqueous phase is washed with methylene chloride and the combined organic layers are dried over sodium sulfate. The solvent is removed under reduced pressure and the residue is purified by preparative HPLC to give the title compound as a white solid: (M−1)−=261.

Workup

  1. additionIce is added
  2. washthe organic phase is washed with 1N HCl
  3. washThe aqueous phase is washed with methylene chloride
  4. dry with materialthe combined organic layers are dried over sodium sulfate
  5. customThe solvent is removed under reduced pressure
  6. customthe residue is purified by preparative HPLC

Sources & evidence

ORD record
ord-f6f8faa5491345ae9425ad18de3add47
Source dataset
uspto-grants-2011_12
Patent number
US08084448B2

Reaction notes

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