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

HRID 244334Notes

Reaction equation

HRID 244334 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). While stirring under ice-cooling, a solution of N-bromosuccinimide (701.28 g, 3.94 mol) in acetonitrile (5 L) was added thereto dropwise. The temperature of the resultant mixture was raised to room temperature, and then the solvent was concentrated to about 3 L. n-Heptane (5 L) and water (5 L) were added thereto for extraction and liquid separation. The aqueous layer was further extracted with n-heptane (2 L) and separated into layers. The organic layer was mixed with the previously obtained organic layer, washed with aqueous solution of 5% sodium thiosulfate (1 L) and water (2 L), and concentrated under reduced pressure (35° C.) to give 977.0 g of the captioned compound as a slightly brown oily material (yield: 99.1%; HPLC purity: 95.8%).

Workup

  1. temperaturecooling
  2. concentrationthe solvent was concentrated to about 3 L
  3. additionn-Heptane (5 L) and water (5 L) were added
  4. extractionfor extraction and liquid separation
  5. extractionThe aqueous layer was further extracted with n-heptane (2 L)
  6. customseparated into layers
  7. additionThe organic layer was mixed with the previously obtained organic layer
  8. washwashed with aqueous solution of 5% sodium thiosulfate (1 L) and water (2 L)
  9. concentrationconcentrated under reduced pressure (35° C.)

Sources & evidence

ORD record
ord-683f56a3c5514d78ab4de32ac37aac9f
Source dataset
uspto-grants-2014_02
Patent number
US08658620B2

Reaction notes

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