5-Bromo-2-fluoro-3-methylbenzyl alcohol → 5-Bromo-2-fluoro-3-methylbenzaldehyde

HRID 1880433Notes

Reaction equation

HRID 1880433 reaction equation
[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1.[Br:12][C:13]1[CH:14]=[C:15]([CH3:22])[C:16]([F:21])=[C:17]([CH2:19][OH:20])[CH:18]=1>ClCCl>[Br:12][C:13]1[CH:14]=[C:15]([CH3:22])[C:16]([F:21])=[C:17]([CH:18]=1)[CH:19]=[O:20]

Participants

4

Reactant 2

HCID 669205355-Bromo-2-fluoro-3-methylbenzyl alcoholHCID 178418287HCID 178418287, compound

Product 1

HCID 532168945-Bromo-2-fluoro-3-methylbenzaldehyde

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred suspension of pyridinium chlorochromate (3.77 g, 17.1 mmol) and silica gel in 25 ml dichloromethane was added a solution of (5-bromo-2-fluoro-3-methylphenyl)methanol in 25 mL dichloromethane. The reaction was stirred for 30 minutes at room temperature. Added additional silica gel and concentrated to adsorb reaction products onto the silica gel. Flash chromatographed (80 g silica, 5-10% ethyl acetate/hexanes gradient) to yield 2.1 g of 5-bromo-2-fluoro-3-methylbenzaldehyde as a white solid. 1H NMR (400 MHz, CDCl3) δ ppm 2.31 (d, J=2.15 Hz, 3 H) 7.42-7.63 (m, 1 H) 7.77 (dd, J=5.46, 2.34 Hz, 1 H) 10.27 (s, 1 H).

Workup

  1. additionAdded additional silica gel
  2. concentrationconcentrated
  3. customreaction products onto the silica gel
  4. customFlash chromatographed (80 g silica, 5-10% ethyl acetate/hexanes gradient)

Sources & evidence

ORD record
ord-c612016d91a948b5bd350f32a24ccb03
Source dataset
uspto-grants-2012_11
Patent number
US08318762B2

Reaction notes

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