Water → HCID 22672085, compound

HRID 1006558Notes

Reaction equation

HRID 1006558 reaction equation
C[O:2][C:3]1[CH:8]=[C:7]([CH:9]([CH3:11])[CH3:10])[CH:6]=[CH:5][C:4]=1[N:12]([S:16]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)(=[O:18])=[O:17])[C:13](=[O:15])[CH3:14].O>C(Cl)Cl.B(Br)(Br)Br>[C:13]([N:12]([S:16]([C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1)(=[O:17])=[O:18])[C:4]1[CH:5]=[CH:6][C:7]([CH:9]([CH3:11])[CH3:10])=[CH:8][C:3]=1[OH:2])(=[O:15])[CH3:14]

Participants

5

Reactant 2

HCID 962WaterHCID 23378640HCID 23378640, compound

Product 1

HCID 22672085HCID 22672085, compoundYield 70.8%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 25134Boron tribromideSolvent

Conditions

Temperature
10 °C

Procedure

To a solution of 2-(N-acetyl-phenylsulfonylamino)-5-isopropylphenyl methyl ether (2.28 g; prepared in Reference Example 40.) in methylene chloride (15 ml), boron tribromide (1.36 ml) was added at 0° C. The mixture was stirred for 5 hours at 10° C. The reaction mixture was poured into iced water, extracted with ethyl acetate. The organic layer was washed, dried over and concentrated. The residue was purified on silica gel column chromatography (benzene:AcOEt=23:2) and recrystallized from AcOEt-hexane mixture solution to give the title compound (1.55 g) having the following physical data.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed
  3. customdried over and
  4. concentrationconcentrated
  5. customThe residue was purified on silica gel column chromatography (benzene:AcOEt=23:2)
  6. customrecrystallized from AcOEt-hexane mixture solution

Sources & evidence

ORD record
ord-236069b24375482ab2a1727fec1634f2
Source dataset
uspto-grants-2004_09
Patent number
US06790866B2

Reaction notes

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