Chlorosuccinimide → 5-Bromo-2-(phenethyl)benzaldehyde

HRID 355759Notes

Reaction equation

HRID 355759 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[C:6]([CH:14]=1)[CH2:7]NC(C)(C)CO.ClN1C(=[O:29])CCC1=O>ClCCl>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[C:6]([CH:14]=1)[CH:7]=[O:29]

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 226755732-(N-(5-bromo-2-(phenethyl)benzyl)amino)-2-methylpropan-1-ol

Product 1

HCID 226754825-Bromo-2-(phenethyl)benzaldehydeYield 48.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 2-(N-(5-bromo-2-(phenethyl)benzyl)amino)-2-methylpropan-1-ol (9.13 g), N-chlorosuccinimide (3.38 g) and dichloromethane (50 ml) was stirred for 4 hours. Aluminia (10 g) was added and the mixture stirred for 6 days, filtered and the solvent evaporated. The residue was dissolved in dichloromethane (200 ml) and alumina (60 g) added in 6 portions over 8 hours. The mixture was filtered, the filtrate evaporated and the residue purified by MPLC eluting with dichloromethane/hexane (1:1) to give 5-bromo-2-(phenethyl)benzaldehyde (3.54 g).

Workup

  1. additionAluminia (10 g) was added
  2. stirringthe mixture stirred for 6 days
  3. filtrationfiltered
  4. customthe solvent evaporated
  5. dissolutionThe residue was dissolved in dichloromethane (200 ml)
  6. additionalumina (60 g) added in 6 portions over 8 hours
  7. filtrationThe mixture was filtered
  8. customthe filtrate evaporated
  9. customthe residue purified by MPLC
  10. washeluting with dichloromethane/hexane (1:1)

Sources & evidence

ORD record
ord-faed92832bb54544aeab3670c13f2323
Source dataset
uspto-grants-1998_11
Patent number
US05834468

Reaction notes

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