Hydrogen Peroxide → HCID 57962486, compound

HRID 541934Notes

Reaction equation

HRID 541934 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([NH:10][C:11](=[O:17])[O:12][C:13]([CH3:16])([CH3:15])[CH3:14])[CH:5]=[C:6]([CH:8]=[CH2:9])[CH:7]=1.B1C2CCCC1CCC2.[OH-:27].[Na+].OO>O1CCCC1.[Cl-].[Na+].O.C(O)C>[Br:1][C:2]1[CH:3]=[C:4]([NH:10][C:11](=[O:17])[O:12][C:13]([CH3:16])([CH3:15])[CH3:14])[CH:5]=[C:6]([CH2:8][CH2:9][OH:27])[CH:7]=1

Participants

8

Reactant 4

HCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 789669-Borabicyclo(3.3.1)nonaneHCID 57961535HCID 57961535, compound

Product 1

HCID 57962486HCID 57962486, compound

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent2×HCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
0 °C

Procedure

A solution of tert-butyl (3-bromo-5-vinylphenyl)carbamate (0.80 g, 2.7 mmol) in tetrahydrofuran (2.7 mL) was treated with 9-BBN in tetrahydrofuran (16.1 mL, 8.1 mol) dropwise and stirred for 2 h. The reaction mixture was cooled to 0° C. and treated with ethanol (5 mL), 3 M sodium hydroxide (3.2 mL) and 9 M hydrogen peroxide (3 mL) dropwise. The reaction mixture was heated at 50° C. for 30 min, cooled to 20° C., poured into brine (25 mL), and extracted with ethyl acetate (100 mL). A small amount of water was added to dissolve the solids that were insoluble in the brine. The organic layer was separated and washed with brine (25 mL), dried over anhydrous sodium sulfate, filtered, and evaporated to give the desired product as a crude tan oil. This material was purified by flash column chromatography to give the desired product (0.66 g, 78%) as a colorless foam. LCMS for C9H11BrNO3 ([M-(t-Bu)+H]+H)+: m/z=259.9, 261.8.

Workup

  1. temperatureThe reaction mixture was heated at 50° C. for 30 min
  2. temperaturecooled to 20° C.
  3. extractionextracted with ethyl acetate (100 mL)
  4. additionA small amount of water was added
  5. dissolutionto dissolve the solids that
  6. customThe organic layer was separated
  7. washwashed with brine (25 mL)
  8. dry with materialdried over anhydrous sodium sulfate
  9. filtrationfiltered
  10. customevaporated

Sources & evidence

ORD record
ord-187c77bc6f0b42799f08d8bb46939dfa
Source dataset
uspto-grants-2014_10
Patent number
US08871753B2

Reaction notes

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