Hydrogen Peroxide → 3-(6-Bromo-2-((tert-butyldimethylsilyl)oxy)-3-chloro-4-(4-methoxybenzyl)phenyl)propan-1-ol

HRID 576403Notes

Reaction equation

HRID 576403 reaction equation
[CH2:1]([C:4]1[C:17]([Br:18])=[CH:16][C:15]([CH2:19][C:20]2[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][CH:21]=2)=[C:14]([Cl:28])[C:5]=1[O:6][Si:7]([C:10]([CH3:13])([CH3:12])[CH3:11])([CH3:9])[CH3:8])[CH:2]=[CH2:3].CSC.B.[OH-:33].[Na+].OO>C1COCC1.O>[Br:18][C:17]1[C:4]([CH2:1][CH2:2][CH2:3][OH:33])=[C:5]([O:6][Si:7]([C:10]([CH3:13])([CH3:12])[CH3:11])([CH3:8])[CH3:9])[C:14]([Cl:28])=[C:15]([CH2:19][C:20]2[CH:21]=[CH:22][C:23]([O:26][CH3:27])=[CH:24][CH:25]=2)[CH:16]=1

Participants

7

Reactant 4

HCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 12423031(Dimethyl sulfide)trihydroboronHCID 86714082(2-Allyl-3-bromo-6-chloro-5-(4-methoxybenzyl)phenoxy)(tert-butyl)dimethylsilane

Product 1

HCID 867140833-(6-Bromo-2-((tert-butyldimethylsilyl)oxy)-3-chloro-4-(4-methoxybenzyl)phenyl)propan-1-olYield 65%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of bromide 186 (2.57 g, 5.33 mmol) in THF (35 mL) was added borane dimethylsulfide complex (10M in THF, 0.18 mL, 1.76 mmol) at 0° C. The mixture was stirred at rt for 1 hr. The mixture was cooled to 0° C. and H2O (0.5 mL), aq. 3N NaOH solution (1.1 mL), 35% H2O2 (0.65 mL) were added to the mixture.) The mixture was stirred at 50° C. for 30 min and cooled to rt. The mixture was extracted with EtOAc/aq. 50% NaCl solution (100 mL/100 mL). The organic layer was washed with brine, dried over MgSO4, filtered and concentrated in vacuo. The residue was purified by silica gel column chromatography to provide the product 187 (1.73 g, 65%).

Workup

  1. temperatureThe mixture was cooled to 0° C.
  2. stirring) The mixture was stirred at 50° C. for 30 min
  3. temperaturecooled to rt
  4. extractionThe mixture was extracted with EtOAc/aq
  5. washThe organic layer was washed with brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-0135ba4ff9824129a752feb07967fa9e
Source dataset
uspto-grants-2015_05
Patent number
US09034921B2

Reaction notes

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