HCID 15900019, compound → 4-Bromo-2-ethylbenzaldehyde

HRID 2387078Notes

Reaction equation

HRID 2387078 reaction equation
[NH+]1([O-])CCOCC1.[Br:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][OH:16])=[C:11]([CH2:17][CH3:18])[CH:10]=1>ClCCl.[Ru]([O-])(=O)(=O)=O.C([N+](CCC)(CCC)CCC)CC>[Br:8][C:9]1[CH:14]=[CH:13][C:12]([CH:15]=[O:16])=[C:11]([CH2:17][CH3:18])[CH:10]=1

Participants

5

Reactant 2

HCID 15900019HCID 15900019, compoundHCID 587642724-bromo-2-ethylbenzenemethanol

Product 1

HCID 532567934-Bromo-2-ethylbenzaldehydeYield 110.8%

Reagents, catalysts & solvents 2

HCID 178419074HCID 178419074, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

Morpholine-N-oxide (5.0 g, 43 mmol) was stirred in dichloromethane (30 mL) over 3A sieves 30 min under N2 atmosphere. (4-Bromo-2-ethyl-phenyl)-methanol (3.1 g, 14.4 mmol), then tetrapropylammonium perruthenate (250 mg, 0.72 mmol) was added. The solution was stirred 2 h then filtered through a plug of silica. The silica was washed with 30% ethyl acetate in hexanes, and the organics were pooled. The solution was concentrated in vacuo to give a light yellow oil (3.4 g). 1H NMR (300 MHz, CDCl3): δ ppm 1.28 (t, J=7.54 Hz, 3 H) 3.04 (q, J=7.54 Hz, 2 H) 7.47 (d, J=1.70 Hz, 1 H) 7.49-7.53 (m, 1 H) 7.69 (d, J=8.29 Hz, 1 H) 10.23 (s, 1 H).

Workup

  1. filtrationthen filtered through a plug of silica
  2. washThe silica was washed with 30% ethyl acetate in hexanes
  3. concentrationThe solution was concentrated in vacuo

Sources & evidence

ORD record
ord-4d950bcfcc8c4bde9b970a4356bde6e7
Source dataset
uspto-grants-2012_09
Patent number
US08268835B2

Reaction notes

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