Triacetoxyperiodinane → 2-Bromo-3,4-difluorobenzaldehyde

HRID 63690Notes

Reaction equation

HRID 63690 reaction equation
[Br:1][C:2]1[C:7]([F:8])=[C:6]([F:9])[CH:5]=[CH:4][C:3]=1[CH2:10][OH:11].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>ClCCl.CCOC(C)=O.C(Cl)Cl>[Br:1][C:2]1[C:7]([F:8])=[C:6]([F:9])[CH:5]=[CH:4][C:3]=1[CH:10]=[O:11]

Participants

5

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 69798476(2-Bromo-3,4-difluorophenyl)methanol

Product 1

HCID 577551402-Bromo-3,4-difluorobenzaldehydeYield 119.1%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 21226138Dichloromethane ethylacetateSolvent

Procedure

(2-Bromo-3,4-difluorophenyl)methanol (Compound AR) (2.55 g, 11.4 mmol, Eq: 1.00) was dissolved in dichloromethane (15 ml). Dess-Martin periodinane (4.85 g, 11.4 mmol, Eq: 1.00) was added. The reaction mixture was stirred for 2 hrs at room temperature. The reaction mixture was filtered over a plug of celite and washed with DCM (30 ml). Filtrate was concentrated to give a semi solid. Crude product was dissolved in EtOAc/DCM and loaded into a silica gel column (4 g). Silica gel column was flushed with EtOAc to give a light yellow solid (3 g). 1H NMR (DMSO) δ 10.13 (s, 1H), 7.74-7.82 (m, 1H), 7.70 (ddd, J=9.5, 7.3, 0.8 Hz, 1H).

Workup

  1. filtrationThe reaction mixture was filtered over a plug of celite
  2. washwashed with DCM (30 ml)
  3. concentrationFiltrate was concentrated
  4. customto give a semi solid
  5. customSilica gel column was flushed with EtOAc

Sources & evidence

ORD record
ord-f7375c218ef149f2866251ce8258f819
Source dataset
uspto-grants-2016_09
Patent number
US09447086B2

Reaction notes

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