N-bromobutanimide → 1-(3-Bromo-5-tert-butyl-4-hydroxyphenyl)ethanone

HRID 2223762Notes

Reaction equation

HRID 2223762 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([C:12](=[O:14])[CH3:13])[CH:8]=[CH:9][C:10]=1[OH:11])([CH3:4])([CH3:3])[CH3:2].[Br:15]N1C(=O)CCC1=O>C(#N)C>[Br:15][C:9]1[C:10]([OH:11])=[C:5]([C:1]([CH3:4])([CH3:2])[CH3:3])[CH:6]=[C:7]([C:12](=[O:14])[CH3:13])[CH:8]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 137241451-(3-Tert-butyl-4-hydroxyphenyl)ethanone

Product 1

HCID 230937111-(3-Bromo-5-tert-butyl-4-hydroxyphenyl)ethanoneYield 99.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

1-(3-tert-Butyl-4-hydroxyphenyl)ethanone (690.9 g, 3.75 mol) was dissolved in acetonitrile (6.05 L), and a solution of N-bromosuccinimide (701.28 g, 3.94 mol) in acetonitrile (5 L) was added dropwise while stirring on ice. After heating to room temperature, the solvent was concentrated to approximately 3 L. For extraction, n-heptane (5 L) and water (5 L) were added, and the solution was separated. The aqueous layer was extracted further with n-heptane (2 L), and the solution was separated. The organic layers were combined, washed with 5% aqueous sodium thiosulfate (1 L) and water (2 L), and concentrated under reduced pressure (35° C.) to obtain 977.0 g of the subject compound as a brownish oily substance (yield: 99.1%, HPLC purity: 95.8%).

Workup

  1. concentrationthe solvent was concentrated to approximately 3 L
  2. extractionFor extraction, n-heptane (5 L) and water (5 L)
  3. additionwere added
  4. customthe solution was separated
  5. extractionThe aqueous layer was extracted further with n-heptane (2 L)
  6. customthe solution was separated
  7. washwashed with 5% aqueous sodium thiosulfate (1 L) and water (2 L)
  8. concentrationconcentrated under reduced pressure (35° C.)

Sources & evidence

ORD record
ord-e5fb82a58c794143b49b7c97a1198806
Source dataset
uspto-grants-2008_05
Patent number
US07375236B2

Reaction notes

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