Sodium Sulfite → tert-Butyl 3-bromo-5-(trifluoroacetyl)benzoate

HRID 888418Notes

Reaction equation

HRID 888418 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:12]=[C:13]([CH:15]([OH:20])[C:16]([F:19])([F:18])[F:17])[CH:14]=1)[C:5]([O:7][C:8]([CH3:11])([CH3:10])[CH3:9])=[O:6].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C1=CC=CC=2)=O.C([O-])(O)=O.[Na+].[O-]S([O-])=O.[Na+].[Na+]>ClCCl>[Br:1][C:2]1[CH:3]=[C:4]([CH:12]=[C:13]([C:15](=[O:20])[C:16]([F:18])([F:19])[F:17])[CH:14]=1)[C:5]([O:7][C:8]([CH3:11])([CH3:9])[CH3:10])=[O:6]

Participants

6

Reactant 4

HCID 24437Sodium SulfiteHCID 159087TriacetoxyperiodinaneHCID 516892Sodium BicarbonateHCID 59539580Tert-butyl 3-bromo-5-(2,2,2-trifluoro-1-hydroxyethyl)benzoate

Product 1

HCID 68496903tert-Butyl 3-bromo-5-(trifluoroacetyl)benzoate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 3-bromo-5-(2,2,2-trifluoro-1-hydroxyethyl)benzoate (8.8 g, 24.8 mmol) in dichloromethane (124 mL) was added Dess-MartinPeriodinane (15.8 g, 37.2 mmol). The mixture was stirred at ambient temperature. After 2 h, saturated NaHCO3 and saturated Na2SO3. The mixture was extracted with dichloromethane (3×). The combined organic extracts were washed with water (6×), brine, dried over sodium sulfate, filtered and concentrated.

Workup

  1. extractionThe mixture was extracted with dichloromethane (3×)
  2. washThe combined organic extracts were washed with water (6×), brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-c30d4ff8585843fdb96109a92ad92318
Source dataset
uspto-grants-2012_08
Patent number
US08247401B2

Reaction notes

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