Triacetoxyperiodinane → (3-Bromophenyl)acetaldehyde

HRID 517530Notes

Reaction equation

HRID 517530 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH2:8][CH2:9][OH:10])[CH:5]=[CH:6][CH:7]=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)Cl>[Br:1][C:2]1[CH:3]=[C:4]([CH2:8][CH:9]=[O:10])[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 27340902-(3-Bromophenyl)ethan-1-ol

Product 1

HCID 20387554(3-Bromophenyl)acetaldehydeYield 57.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-(3-bromophenyl)ethanol (9.0 g, 0.044 mol) in DCM (300 mL), Dess-Martin reagent (38.0 g, 0.090 mol) was added in portions. The reaction mixture was stirred overnight, and filtered. The filtrate was evaporated, and the residue was purified by silica gel column chromatography (Petroleum ether:EtOAc=5:1) to afford 2-(3-bromophenyl)acetaldehyde (5.0 g, 55%) as a yellow oil. MS (ES+) C8H7BrO requires: 198, 200 found: 199 [M+H]+, 201 [M+2+H]+(1:1).

Workup

  1. filtrationfiltered
  2. customThe filtrate was evaporated
  3. customthe residue was purified by silica gel column chromatography (Petroleum ether:EtOAc=5:1)

Sources & evidence

ORD record
ord-555a09d83b50438eabc220b10be8db95
Source dataset
uspto-grants-2015_08
Patent number
US09115120B2

Reaction notes

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