Sodium Hydroxide → 2-Bromo-4-(trifluoromethyl)benzaldehyde

HRID 1810492Notes

Reaction equation

HRID 1810492 reaction equation
[Br:1][C:2]1[CH:9]=[C:8]([C:10]([F:13])([F:12])[F:11])[CH:7]=[CH:6][C:3]=1[CH2:4][OH:5].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[OH-].[Na+]>C(Cl)Cl.C([O-])([O-])=O.[Na+].[Na+]>[Br:1][C:2]1[CH:9]=[C:8]([C:10]([F:11])([F:12])[F:13])[CH:7]=[CH:6][C:3]=1[CH:4]=[O:5]

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 159087TriacetoxyperiodinaneHCID 2779289[2-Bromo-4-(trifluoromethyl)phenyl]methanol

Product 1

HCID 30203732-Bromo-4-(trifluoromethyl)benzaldehyde

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 10340Sodium CarbonateSolvent2×

Procedure

2-Bromo-4-(trifluoromethyl)benzyl alcohol (4.0 g, 15.88 mmol) and Dess-Martin periodinane (7.14 g, 16.67 mmol) were combined in CH2Cl2 and stirred for 1.5 hours at room temperature. Saturated aqueous Na2CO3 was added, and a white precipitate was formed. The mixture was diluted with CH2Cl2 and saturated aqueous Na2CO3 and stirred for 1 hour. 1N Aqueous NaOH was added, and the organic layer was separated and concentrated. The residue was purified by silica gel chromatography (0-80% EtOAc in hexanes) to give the title compound.

Workup

  1. customa white precipitate was formed
  2. stirringstirred for 1 hour
  3. customthe organic layer was separated
  4. concentrationconcentrated
  5. customThe residue was purified by silica gel chromatography (0-80% EtOAc in hexanes)

Sources & evidence

ORD record
ord-181a531663a44e69b66a3cd30f9923e7
Source dataset
uspto-grants-2013_01
Patent number
US08362044B2

Reaction notes

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