Triacetoxyperiodinane → 2-Bromo-5-chloro-4-(4-ethylbenzyl)benzaldehyde

HRID 1716969Notes

Reaction equation

HRID 1716969 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([CH2:8][C:9]2[CH:14]=[CH:13][C:12]([CH2:15][CH3:16])=[CH:11][CH:10]=2)[C:5]([Cl:17])=[CH:4][C:3]=1[CH2:18][OH:19].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>ClCCl>[Br:1][C:2]1[CH:7]=[C:6]([CH2:8][C:9]2[CH:14]=[CH:13][C:12]([CH2:15][CH3:16])=[CH:11][CH:10]=2)[C:5]([Cl:17])=[CH:4][C:3]=1[CH:18]=[O:19]

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 59467877(2-Bromo-5-chloro-4-(4-ethylbenzyl)phenyl)methanol

Product 1

HCID 590134742-Bromo-5-chloro-4-(4-ethylbenzyl)benzaldehyde

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a cooled solution (−5° C.) of (2-bromo-5-chloro-4-(4-ethylbenzyl)phenyl)methanol (9.7 g, 29.4 mmol) in dry dichloromethane (100 mL), was added dropwise a solution of Dess-Martin reagent (18.7 g, 44 mmol) in 100 mL of dry dichloromethane. After it was stirred at room temperature for 2 h, TLC showed the reaction was complete. The reaction was quenched by addition of 10 mL of 1 M NaOH. The organic layer was washed 1× with NaHSO3, 2× with NaHCO3, 3× with brine, dried over anhydrous Na2SO4. Concentration under reduced pressure provided the pure product as a white solid. Yield: 9.3 g (96%). 1H NMR (CDCl3, 300 MHz) δ 10.24 (s, 1H), 7.91 (s, 1H), 7.40 (s, 1H), 7.18 (s, 1H), 7.15 (s, 1H), 7.11 (s, 1H), 7.09 (s, 1H), 4.08 (s, 2H), 4.02 (s, 2H), 2.63 (q, J=7.8 Hz, 2H), 1.23 (t, J=7.8 Hz, 3H).

Workup

  1. customThe reaction was quenched by addition of 10 mL of 1 M NaOH
  2. washThe organic layer was washed 1× with NaHSO3, 2× with NaHCO3, 3× with brine
  3. dry with materialdried over anhydrous Na2SO4
  4. concentrationConcentration under reduced pressure

Sources & evidence

ORD record
ord-5c6f8b57e986423baec9aed8a2b89640
Source dataset
uspto-grants-2010_09
Patent number
US07803778B2

Reaction notes

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