Triacetoxyperiodinane → 5-Bromo-[1,1'-biphenyl]-2-carbaldehyde

HRID 1499125Notes

Reaction equation

HRID 1499125 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:14][OH:15])=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[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:7]=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[C:5]([CH:14]=[O:15])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 1179418105-Bromobiphenyl-2-methanol

Product 1

HCID 541973195-Bromo-[1,1'-biphenyl]-2-carbaldehyde

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (5-bromo-[1,1′-biphenyl]-2-yl)methanol (2.0 g, 8.4 mmol) in CH2Cl2 (30 mL) was added Dess-Martin Periodinane (4.3 g, 10 mmol). The reaction mixture was stirred at RT for 2 h and then the solids were filtered and the resultant filtrate was concentrated in vacuo. Purification by normal phase silica gel column (EtOAc:PE=1:50) afforded 5-bromo-[1,1′-biphenyl]-2-carbaldehyde as a colorless oil.

Workup

  1. filtrationthe solids were filtered
  2. concentrationthe resultant filtrate was concentrated in vacuo
  3. customPurification by normal phase silica gel column (EtOAc:PE=1:50)

Sources & evidence

ORD record
ord-1d0a536df2074e7e82c63780d3c40bf4
Source dataset
uspto-grants-2015_12
Patent number
US09199994B2

Reaction notes

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